Heterocyclic compounds and noxious arthropod control agent containing same

ABSTRACT

A compound of formula (C-7),wherein RQ represents a fluorine atom, a chlorine atom, or a —S(O)nR2; RQ2 represents a —S(O)nR2; R2 represents an ethyl group; n represents 0, 1, or 2; R3b represents a chlorine atom; and R3c represents a hydrogen atom.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. patent application Ser. No.16/957,264, filed Jun. 23, 2020, which is a Section 371 of InternationalApplication No. PCT/JP2018/047466, filed Dec. 25, 2018, which is basedupon and claims the benefit of priority to Japanese Application No.2017-247334, filed Dec. 25, 2017. The entire contents of all of theabove applications are incorporated herein by reference.

TECHNICAL FIELD

This application claims the priority to and the benefit of JapanesePatent Application No. 2017-247334 filed on Dec. 25, 2017, the entirecontents of which are incorporated herein by reference.

The present invention relates to heterocyclic compounds and agents forcontrolling harmful arthropods comprising the same.

BACKGROUND ART

To date, various compounds have been studied in order to control harmfularthropods. For example, Patent Document 1 discloses that certain kindsof compound have control effects on pests.

CITATION LIST Patent Document

-   Patent Document 1: WO 2013/191112 pamphlet SUMMARY OF THE INVENTION

Problems to be Solved by Invention

An object of the present invention is to provide compounds havingexcellent control efficacy against harmful arthropods.

Means to Solve Problems

The present invention provides the followings.

-   [1] A compound represented by formula (I)

-   [wherein:

Q represents a group represented by Q1 or a group represented by Q2;

Z represents an oxygen atom or a sulfur atom;

A¹ represents a nitrogen atom or a CR⁵;

R⁵ represents a halogen atom or a hydrogen atom;

A² and A³ represents a combination, which is

a combination wherein A² represents a CR^(4a) and A³ represents anitrogen atom or a CR^(4b); or

a combination wherein A² represents a nitrogen atom and A³ represents aCR4;

B¹, B², and B³ represents a combination, which is

a combination wherein B¹ represents a CR¹, B² represents a nitrogen atomor a CR^(6b), and B³ represents a nitrogen atom or a CR^(6c);

a combination wherein B represents a nitrogen atom or a CR^(6a), B²represents a CR¹, and B³ represents a nitrogen atom or a CR^(6c); or

a combination wherein B¹ represents a nitrogen atom or a CR^(6a), B²represents a nitrogen atom or a CR^(6b), and B³ represents a CR¹;

R¹ represents a C1-C6 chain hydrocarbon group having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom, a C3-C4 cycloalkyl group optionally having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom, a —SR⁸, a —S(O)R⁸, a —S(O)₂R, a —OR⁸, or a —OS(O)₂R⁸;

R⁸ represents a C1-C6 chain hydrocarbon group having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom, or a C3-C4 cycloalkyl group optionally having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom;

R^(4a), R^(4b), R^(6a), R^(6b), and R^(6c) are identical to or differentfrom each other, and each represent a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atom(s), a C3-C7 cycloalkyl groupoptionally having one or more halogen atom(s), a C1-C6 alkoxy groupoptionally having one or more halogen atom(s), a —NR⁹R¹⁰, a —C(O)R⁷, a—C(O)OR⁷, a —C(O)NR¹⁹R²⁰, a —NR⁹C(O)R¹⁸, a —NR⁹C(O)OR¹⁸, a—NR⁹C(O)NR¹⁹R²⁰, a cyano group, a halogen atom, or a hydrogen atom;

R⁹ and R¹⁹ are identical to or different from each other, and eachrepresent a C1-C6 chain hydrocarbon group optionally having one or morehalogen atom(s), or a hydrogen atom;

R¹⁰ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituent(s) selected from Group F, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group J, aC3-C7 cycloalkenyl group optionally having one or more substituent(s)selected from Group J, a phenyl group optionally having one or moresubstituent(s) selected from Group D, a 6 membered aromatic heterocyclicgroup optionally having one or more substituent(s) selected from GroupD, a hydrogen atom, or a —S(O)₂R²¹;

R²¹ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), a C3-C7 cycloalkyl group optionally having one ormore halogen atom(s), or a phenyl group optionally having one or moresubstituent(s) selected from Group D;

R⁷, R¹⁸, and R²⁰ are identical to or different from each other, and eachrepresent a C1-C6 chain hydrocarbon group optionally having one or moresubstituent(s) selected from Group F, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group J, or ahydrogen atom;

R² represents a C1-C6 chain hydrocarbon group optionally substitutedwith one or more halogen atom(s), a cyclopropyl group, or acyclopropylmethyl group;

n represents 0, 1, or 2;

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituent(s) selected from Group B, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group E, aC3-C7 cycloalkenyl group optionally having one or more substituent(s)selected from Group J, a phenyl group optionally having one or moresubstituent(s) selected from Group H, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituent(s) selectedfrom Group H, a —OR¹², a —NR¹¹R¹², a —NR^(11a)R^(12a), a —NR²⁴NR¹¹R¹², a—NR²⁴OR¹¹, a —NR¹¹C(O)R³, a —NR²⁴NR¹¹C(O)R¹³, a —NR¹¹C(O)OR¹⁴, a—NR²⁴NR¹¹C(O)OR¹⁴, a —NR¹¹C(O)NR^(15a)R^(16a), a—NR²⁴NR¹¹C(O)NR^(15a)R^(16a), a —N═CR²⁴NR^(15a)R^(16a), a—N═S(O)_(x)R¹⁵R¹⁶, a —C(O)R¹³, a —C(O)OR¹⁷, a —C(O)NR^(15a)R^(16a), a—C(O)NR¹¹S(O)₂R²³, a —CR²⁴═NOR¹⁷, a —NR¹¹CR²⁴═NOR¹⁷, a cyano group, anitro group, or a halogen atom;

q represents 0, 1, 2, or 3, wherein when q represents 2 or 3, two orthree R³ may be identical to or different from each other;

When two R³ are adjacent with each other, the two R³ may be combinedwith the two carbon atoms to which they are attached to form a benzenering, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring,an imidazole ring, a triazole ring, an oxazole ring, an isoxazole ring,a thiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridinering, a pyridazine ring, a pyrimidine ring, or a pyrazine ring {whereinsaid benzene ring, said pyrrole ring, said furan ring, said thiophenering, said pyrazole ring, said imidazole ring, said triazole ring, saidoxazole ring, said isoxazole ring, said thiazole ring, said pyridinering, said pyridazine ring, said pyrimidine ring, and said pyrazine ringmay optionally have one or more substituent(s) selected from Group H};

R¹⁷ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), a phenyl group optionally having one or moresubstituent(s) selected from Group D, or a hydrogen atom;

R¹¹, R^(15a), and R²⁴ are identical to or different from each other, andeach represent a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), or a hydrogen atom;

R¹² represents a C1-C6 chain hydrocarbon group optionally having one ormore substituent(s) selected from Group F, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group J, aC3-C7 cycloalkenyl group optionally having one or more substituent(s)selected from Group J, a phenyl group optionally having one or moresubstituent(s) selected from Group D, a 6 membered aromatic heterocyclicgroup optionally having one or more substituent(s) selected from GroupD, a hydrogen atom, or a —S(O)₂R²³;

R²³ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), a C3-C7 cycloalkyl group optionally having one ormore halogen atom(s), or a phenyl group optionally having one or moresubstituent(s) selected from Group D;

R^(11a) and R^(12a) may be combined with the nitrogen atom to which theyare attached to form a 3-7 membered nonaromatic heterocyclic groupoptionally having one or more substituent(s) selected from Group E;

R¹³ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), a C3-C7 cycloalkyl group optionally having one ormore halogen atom(s), a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atom(s), a phenyl group optionally having oneor more substituent(s) selected from Group D, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituent(s) selectedfrom Group D, or a hydrogen atom;

R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atom(s), a C3-C7 cycloalkyl group optionally having one ormore halogen atom(s), a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atom(s), or a (phenyl optionally having oneor more substituent(s) selected from Group D)C1-C3 alkyl group;

R¹⁵ and R¹⁶ are identical to or different from each other, and eachrepresent a C1-C6 alkyl group optionally having one or more halogenatom(s);

R^(16a) represents a C1-C6 chain hydrocarbon group optionally having oneor more substituent(s) selected from Group F, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group J, or ahydrogen atom; and

x represents 0 or 1;

Group B: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atom(s), a C3-C6 alkenyloxy group optionally havingone or more halogen atom(s), a C3-C6 alkynyloxy group optionally havingone or more halogen atom(s), a C1-C6 alkylsulfanyl group optionallyhaving one or more halogen atom(s), a C1-C6 alkylsulfinyl groupoptionally having one or more halogen atom(s), a C1-C6 alkylsulfonylgroup optionally having one or more halogen atom(s), a C3-C6 cycloalkylgroup optionally having one or more halogen atom(s), a (C1-C6 alkyloptionally having one or more halogen atom(s))amino group, a di(C1-C4alkyl)amino group optionally having one or more halogen atom(s), a C2-C6alkylcarbonyl group optionally having one or more halogen atom(s), aC2-C6 alkoxycarbonyl group optionally having one or more halogenatom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or morehalogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionallyhaving one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4alkyl)amino optionally having one or more halogen atom(s))carbonylgroup, a (C2-C6 alkoxycarbonyl optionally having one or more halogenatom(s))amino group, a (C2-C6 alkoxycarbonyl) (C1-C6 alkyl)amino groupoptionally having one or more halogen atom(s), a cyano group, an aminogroup, a nitro group, a hydroxy group, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atom(s), a C1-C6 alkoxy groupoptionally having one or more halogen atom(s), a C3-C6 alkenyloxy groupoptionally having one or more halogen atom(s), a C3-C6 alkynyloxy groupoptionally having one or more halogen atom(s), a C1-C6 alkylsulfanylgroup optionally having one or more halogen atom(s), a C1-C6alkylsulfinyl group optionally having one or more halogen atom(s), aC1-C6 alkylsulfonyl group optionally having one or more halogen atom(s),a C3-C6 cycloalkyl group optionally having one or more halogen atom(s),a (C1-C6 alkyl optionally having one or more halogen atom(s))aminogroup, a di(C1-C4 alkyl)amino group optionally having one or morehalogen atom(s), a C2-C6 alkylcarbonyl group optionally having one ormore halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having oneor more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionallyhaving one or more halogen atom(s), an aminocarbonyl group, a (C1-C6alkyl optionally having one or more halogen atom(s))aminocarbonyl group,a (di(C1-C4 alkyl)amino optionally having one or more halogenatom(s))carbonyl group, a (C2-C6 alkoxycarbonyl optionally having one ormore halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl) (C1-C6alkyl)amino group optionally having one or more halogen atom(s), a cyanogroup, an amino group, a nitro group, a hydroxy group, and a halogenatom;

Group E: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atom(s), a C1-C6 alkoxy groupoptionally having one or more halogen atom(s), a C3-C6 alkenyloxy groupoptionally having one or more halogen atom(s), a C3-C6 alkynyloxy groupoptionally having one or more halogen atom(s), a (C1-C6 alkyl optionallyhaving one or more halogen atom(s))amino group, a di(C1-C4 alkyl)aminogroup optionally having one or more halogen atom(s), a C2-C6alkylcarbonyl group optionally having one or more halogen atom(s), aC2-C6 alkoxycarbonyl group optionally having one or more halogenatom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or morehalogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionallyhaving one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4alkyl)amino optionally having one or more halogen atom(s))carbonylgroup, a (C2-C6 alkoxycarbonyl optionally having one or more halogenatom(s))amino group, a (C2-C6 alkoxycarbonyl) (C1-C6 alkyl)amino groupoptionally having one or more halogen atom(s), a cyano group, an aminogroup, a nitro group, a hydroxy group, an oxo group, and a halogen atom;

Group F: a group consisting of a C3-C6 cycloalkyl group optionallyhaving one or more halogen atom(s), a phenyl group optionally having oneor more substituent(s) selected from Group D, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituent(s) selectedfrom Group D, a C1-C6 alkoxy group optionally having one or more halogenatom(s), a (C1-C6 alkyl optionally having one or more halogenatom(s))amino group, a di(C1-C4 alkyl)amino group optionally having oneor more halogen atom(s), a cyano group, an amino group, a nitro group, ahydroxy group, and a halogen atom;

Group H: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atom(s), a C3-C6 cycloalkyl groupoptionally having one or more halogen atom(s), a phenyl group optionallyhaving one or more substituent(s) selected from Group D, a 5 or 6membered aromatic heterocyclic group optionally having one or moresubstituent(s) selected from Group D, a C1-C6 alkoxy group optionallyhaving one or more halogen atom(s), a (C1-C6 alkyl optionally having oneor more halogen atom(s))amino group, a di(C1-C4 alkyl)amino groupoptionally having one or more halogen atom(s), a C2-C6 alkylcarbonylgroup optionally having one or more halogen atom(s), a C2-C6alkoxycarbonyl group optionally having one or more halogen atom(s), aC2-C6 alkoxycarbonyloxy group optionally having one or more halogenatom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally having one ormore halogen atom(s))aminocarbonyl group, a (di(C1-C4 alkyl)aminooptionally having one or more halogen atom(s))carbonyl group, a (C2-C6alkoxycarbonyl optionally having one or more halogen atom(s))aminogroup, a (C2-C6 alkoxycarbonyl) (C1-C6 alkyl)amino group optionallyhaving one or more halogen atom(s), a cyano group, an amino group, anitro group, a hydroxy group, and a halogen atom;

Group J: a group consisting of a C1-C6 alkyl group optionally having oneor more halogen atom(s), a C1-C6 alkoxy group optionally having one ormore halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having oneor more halogen atom(s), an amino group, a cyano group, and a halogenatom]

or an N-oxide compound thereof (hereinafter the compound represented byformula (I) or N-oxide compound thereof is referred to as “Presentcompound X”).

-   [2] The compound represented by formula (I) according to-   [1] (hereinafter referred to as “Present compound”).-   [3] The compound according to [1] or [2], wherein A¹ represents a    CH.-   [4] The compound according to [1] or [2], wherein A¹ represents a    nitrogen atom.-   [5] The compound according to any one of [1] to [4], wherein Q    represents the group represented by Q1.-   [6] The compound according to any one of [1] to [4], wherein Q    represents the group represented by Q2.-   [7] The compound according to any one of [1] to [6], wherein R¹    represents a C1-C6 alkyl group having one or more substituent(s)    selected from the group consisting of a cyano group and a halogen    atom, a cyclopropyl group optionally having one or more    substituent(s) selected from the group consisting of a cyano group    and a halogen atom, or a —OS(O)₂R⁸.-   [8] The compound according to any one of [1] to [7], wherein R³    represents a C1-C6 alkyl group optionally having one or more    substituent(s) selected from Group B, a C3-C7 cycloalkyl group    optionally having one or more substituent(s) selected from Group E,    a phenyl group optionally having one or more substituent(s) selected    from Group J, a 5 membered aromatic heterocyclic group comprising 1    to 4 nitrogen atom(s) optionally having one or more substituent(s)    selected from Group J, a 6 membered aromatic heterocyclic group    optionally having one or more substituent(s) selected from Group J,    a —OR¹², a —NR¹¹R¹², a —NR¹¹C(O)OR¹⁴, or a halogen atom.-   [9] The compound according to any one of [1] to [8], wherein R²    represents an ethyl group.-   [10] The compound according to any one of [1] to [9], wherein Z    represents an oxygen atom.-   [11] A composition for controlling a harmful arthropod comprising    the compound according to any one of [1] to [10] and an inert    carrier.-   [12] A method for controlling a harmful arthropod which comprises    applying an effective amount of the compound according to any one of    [1] to [10] to a harmful arthropod or a habitat where a harmful    arthropod lives.-   [13] A composition comprising one or more ingredient(s) selected    from the group consisting of Group (a) and Group (b), and the    compound according to any one of [1] to [10]:

Group (a): a group consisting of insecticidal active ingredients,miticidal active ingredients, and nematicidal active ingredients;

Group (b): fungicidal active ingredients.

-   [14] A method for controlling a harmful arthropod which comprises    applying an effective amount of the composition according to [13] to    a harmful arthropod or a habitat where a harmful arthropod lives.-   [15] A seed or a vegetative reproduction organ holding an effective    amount of the compound according to any one of-   [1] to [10] or an effective amount of the composition according to    [13].

Effect of Invention

According to the present invention, harmful arthropods can becontrolled.

MODE FOR CARRYING OUT THE INVENTION

The substituents in the present invention are explained as follows.

The term of “halogen atom” represents a fluorine atom, a chlorine atom,a bromine atom, or an iodine atom.

When a substituent has two or more halogen atoms, these halogen atomsmay be identical to or different from each other.

When a substituent has two or more substituents selected from a specificgroup (for example, a group consisting of a cyano group and a halogenatom), these substituents may be identical to or different from eachother.

When a group “optionally having one or more substituent(s) selected fromGroup X” (wherein X represents any one of B, D, E, F, H, and J) asdescribed herein has two or more substituents selected from Group X,these substituents may be identical to or different from each other.

The expression of “CX-CY” as described herein means that the number ofcarbon atom is X to Y. For example, the expression of “C1-C6” means thatthe number of carbon atom is 1 to 6.

The term of “chain hydrocarbon group” represents an alkyl group, analkenyl group, or an alkynyl group.

Examples of the term of “alkyl group” include a methyl group, an ethylgroup, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a1,2-dimethylpropyl group, a butyl group, a tert-butyl group, a pentylgroup, and a hexyl group.

Examples of the term of “alkenyl group” include a vinyl group, a1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 3-butenylgroup, a 4-pentenyl group, and a 5-hexenyl group.

Examples of the term of “alkynyl group” include an ethinyl group, a1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group,and a 5-hexynyl group.

The term of “C1-C3 perfluoroalkyl group” represents a trifluoromethylgroup, a pentafluoroethyl group, a heptafluoropropyl group, or aheptafluoroisopropyl group.

The term of “C1-C2 perfluoroalkyl group” represents a trifluoromethylgroup or a pentafluoroethyl group.

The term of “C1-C3 alkoxy group” represents a methoxy group, an ethoxygroup, a propoxy group, or an isopropoxy group.

Examples of the term of “cycloalkyl group” include a cyclopropyl group,a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and acycloheptyl group.

Examples of the term of “cycloalkenyl group” include a cyclopropenylgroup, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenylgroup, and a cycloheptenyl group.

The term of “3-7 membered nonaromatic heterocyclic group” represents anaziridine ring, an azetidine ring, a pyrrolidine ring, an imidazolinering, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidinering, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, anoxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, amorpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, anisothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a1,4-thiazepane ring. Examples of the 3-7 membered nonaromaticheterocyclic group optionally having one or more substituent(s) selectedfrom Group E include the following groups.

The term of “5 or 6 membered aromatic heterocyclic group” represents a 5membered aromatic heterocyclic group or a 6 membered aromaticheterocyclic group, and the term of “5 membered aromatic heterocyclicgroup” represents a pyrrolyl group, a furyl group, a thienyl group, apyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolylgroup, an oxazolyl group, an isoxazolyl group, a thiazolyl group, anisothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. Theterm of “5 membered aromatic heterocyclic group comprising 1 to 4nitrogen atom(s)” represents a pyrrolyl group, a pyrazolyl group, animidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolylgroup, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, anoxadiazolyl group, or a thiadiazolyl group. The term of “6 memberedaromatic heterocyclic group represents a pyridyl group, a pyridazinylgroup, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or atetrazinyl group.

The term of “(C3-C6 cycloalkyl)C1-C3 alkyl group optionally having oneor more halogen atom(s)” means that the (C3-C6 cycloalkyl) moiety and/orthe (C1-C3 alkyl) moiety may optionally have one or more halogenatom(s), and examples thereof include a cyclopropylmethyl group, a(2-fluorocyclopropyl)methyl group, a cyclopropyl(fluoro)methyl group,and a (2-fluorocyclopropyl) (fluoro)methyl group. The term of “(C2-C6alkoxycarbonyl) (C1-C6 alkyl)amino group optionally having one or morehalogen atom(s)” means that the (C2-C6 alkoxycarbonyl) moiety and/or the(C1-C6 alkyl) moiety may optionally have one or more halogen atom(s),and examples thereof include a (2-fluoroethoxycarbonyl) (methyl)aminogroup, a (methoxycarbonyl) (2-fluoroethyl)amino group, and a(2-fluoroethoxycarbonyl) (2-fluoroethyl)amino group.

The Present compound X may optionally have one or more stereoisomer(s).Examples of the stereoisomer(s) include enantiomers, diastereomers, andgeometric isomers. The present invention encompasses each stereoisomerand mixtures of stereoisomers at any ratio.

The Present compound X may optionally form an acid addition salt.Examples of the acid to form the acid addition salt include inorganicacids such as hydrogen chloride, phosphoric acid, and sulfuric acid; andorganic acids such as acetic acid, trifluoroacetic acid, benzoic acid,and p-toluenesulfonic acid. Such acid addition salt may be prepared bymixing the Present compound X with an acid.

Embodiments of the Present compound include the following compounds.

-   [Embodiment 1] The Present compound, wherein

Z represents an oxygen atom;

R² represents a C1-C6 alkyl group optionally substituted with one ormore halogen atom(s);

A¹ represents a nitrogen atom or a CH; and

R^(4a) and R^(4b) each represent a hydrogen atom.

-   [Embodiment 2] The Present compound, wherein

Z represents an oxygen atom;

R² represents an ethyl group;

A¹ represents a nitrogen atom or a CH; and

R^(4a) and R^(4b) each represent a hydrogen atom.

-   [Embodiment 3] The compound according to Embodiment 2, wherein n    represents 2.-   [Embodiment 4] The Present compound, wherein

Z represents an oxygen atom;

R² represents an ethyl group;

A¹ represents a nitrogen atom;

A² and A³ each represent a CH;

n represents 2; and

q represents 0 or 1.

-   [Embodiment 5] The compound according to Embodiment 4, wherein

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituent(s) selected from Group B, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group E, aphenyl group optionally having one or more substituent(s) selected fromGroup H, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituent(s) selected from Group H, a —OR¹², a —NR¹¹R¹², a—NR¹¹C(O)OR¹⁴, a —NR¹¹C(O)NR^(15a)R^(16a), a —C(O)OR¹⁷, a—C(O)NR^(15a)R^(16a), a cyano group, a nitro group, or a halogen atom.

-   [Embodiment 6] The compound according to Embodiment 4, wherein

R³ represents a C1-C6 alkyl group optionally having one or more halogenatom(s), a cyclopropyl group optionally having a cyano group, a phenylgroup optionally having one or more substituent(s) selected from GroupJ, a 5 or 6 membered aromatic heterocyclic group optionally having oneor more substituent(s) selected from Group J, a —OR¹², a —NR¹¹R¹², a—NR¹¹C(O)OR¹⁴, a —NR¹¹C(O)NR^(15a)R^(16a), a —C(O)OR¹⁷, a—C(O)NR^(15a)R^(16a), or a halogen atom.

-   [Embodiment 7] The compound according to Embodiment 4, wherein

R³ represents a phenyl group optionally having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom, a cyclopropyl group optionally having a cyano group, atrifluoromethyl group, or a halogen atom.

-   [Embodiment 8] The compound according to any one of Embodiments 1 to    7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR^(6c); or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 9] The compound according to any one of Embodiments 1 to    7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 10] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR^(6c); or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 11] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 12] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 13] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 14] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 15] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR^(6c); or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 16] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 17] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR^(6c); or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 18] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 19] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 20] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 21] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 22] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR^(6c); or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 23] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents a combination wherein B²represents a CR¹ and B³ represents a nitrogen atom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 24] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom or a CR⁶C; or

a combination wherein B² represents a nitrogen atom or a CR^(6b) and B³represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a), R^(6b), and R^(6c) are identical to or different from eachother, and each represent a C1-C3 alkyl group optionally having one ormore halogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 25] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom:

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 26] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 27] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a nitrogenatom; or

a combination wherein B² represents a nitrogen atom and B³ represents aCR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 28] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

the combination of B² and B³ represents

a combination wherein B² represents a CR¹ and B³ represents a CH; or

a combination wherein B² represents a CH and B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 29] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 30] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 31] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a CR^(6c);

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 32] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 33] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 34] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 35] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 36] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 37] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 38] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 39] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 40] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 41] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a CR^(6c)—

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 42] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 43] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 44] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 45] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 46] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 47] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 48] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 49] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 50] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 51] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a R^(6c);

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 52] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom or a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 53] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a nitrogen atom;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 54] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR¹;

B³ represents a CR^(6c);

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6c) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 55] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 56] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 57] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 58] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 59] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 60] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 61] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 62] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 63] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 64] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a R^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 65] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

B² represents a nitrogen atom;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 66] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a nitrogen atom;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 67] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

B² represents a nitrogen atom;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 68] The compound according to any one of Embodiments 1    to 7, wherein

B¹ represents a CH;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 69] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR⁶;

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 70] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 71] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 72] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 73] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a)

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 74] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 75] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a nitrogen atom;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 76] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 77] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a nitrogen atom;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 78] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 79] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 80] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 81] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B represents a nitrogen atom or a CR^(6a);

B² represents a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C3 perfluoroalkyl group, a 1-cyanocyclopropyl group,or a 1-cyano-1-methylethyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 82] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a nitrogen atom or a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 83] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a)

B² represents a nitrogen atom;

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) represents a C1-C3 alkyl group optionally having one or morehalogen atom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 84] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom or a CR^(6a);

B² represents a CR^(6b);

B³ represents a CR¹;

R¹ represents a C1-C2 perfluoroalkyl group; and

R^(6a) and R^(6b) are identical to or different from each other, andeach represent a C1-C3 alkyl group optionally having one or more halogenatom(s), a halogen atom, or a hydrogen atom.

-   [Embodiment 85] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a nitrogen atom;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 86] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 87] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a nitrogen atom;

B³ represents a CR; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 88] The compound according to any one of Embodiments 1    to 7, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a CH;

B³ represents a CR¹; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 89] The compound according to any one of Embodiments 1    to 7, wherein Q represents the group represented by Q1.-   [Embodiment 90] The compound according to any one of Embodiments 1    to 7, wherein Q represents the group represented by Q2.

Embodiment of the Present compound X include the following compounds.

-   [Embodiment 91] The Present compound X, wherein

Z represents an oxygen atom;

R² represents a C1-C6 alkyl group optionally substituted with one ormore halogen atom(s);

A¹ represents a nitrogen atom or a CH; and

R^(4a) and R^(4b) each represent a hydrogen atom.

-   [Embodiment 92] The Present compound X, wherein

Z represents an oxygen atom;

R² represents an ethyl group;

A¹ represents a nitrogen atom or a CH; and

R^(4a) and R^(4b) each represent a hydrogen atom.

-   [Embodiment 93] The compound according to Embodiment 92, wherein n    represents 2.-   [Embodiment 94] The Present compound X, wherein

Z represents an oxygen atom;

R² represents an ethyl group;

A¹ represents a nitrogen atom;

A² and A³ each represent a CH;

n represents 2; and

q represents 0 or 1.

-   [Embodiment 95] The compound according to Embodiment 94, wherein

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituent(s) selected from Group B, a C3-C7 cycloalkyl groupoptionally having one or more substituent(s) selected from Group E, aphenyl group optionally having one or more substituent(s) selected fromGroup H, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituent(s) selected from Group H, a —OR¹², a —NR¹¹R¹², a—NR¹¹C(O)OR¹⁴, a —NR¹¹C(O),NR^(15a)R^(16a), a —C(O)OR¹⁷, a—C(O)NR^(15a)R^(16a), a cyano group, a nitro group, or a halogen atom.

-   [Embodiment 96] The compound according to Embodiment 94, wherein

R³ represents a C1-C6 alkyl group optionally having one or more halogenatom(s), a cyclopropyl group optionally having a cyano group, a phenylgroup optionally having one or more substituent(s) selected from GroupJ, a 5 or 6 membered aromatic heterocyclic group optionally having oneor more substituent(s) selected from Group J, a —OR¹², a —NR¹¹R¹², a—NR¹¹C(O)OR¹⁴, a —NR¹¹C(O)NR^(15a)R^(16a), a —C(O)OR¹⁷, a—C(O)NR^(15a)R^(16a), or a halogen atom.

-   [Embodiment 97] The compound according to Embodiment 94, wherein

R³ represents a phenyl group optionally having one or moresubstituent(s) selected from the group consisting of a cyano group and ahalogen atom, a cyclopropyl group optionally having a cyano group, atrifluoromethyl group, or a halogen atom.

-   [Embodiment 98] The compound according to Embodiment 94, wherein

R³ represents a trifluoromethyl group, a cyclopropyl group, a hydroxygroup, a phenyl group optionally having one or more halogen atom(s), aC1-C3 alkoxy group optionally substituted with one or more halogenatom(s), or a halogen atom.

-   [Embodiment 99] The compound according to any one of Embodiments 91    to 98, wherein

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 100] The compound according to any one of Embodiments 91    to 98, wherein

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 101] The compound according to any one of Embodiments 91    to 98, wherein

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 102] The compound according to any one of Embodiments 91    to 98, wherein

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 103] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 104] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q1;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 105] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 106] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q1;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 107] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 108] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q2;

B¹ represents a nitrogen atom;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 109] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a nitrogen atom; and

R¹ represents a C1-C2 perfluoroalkyl group.

-   [Embodiment 110] The compound according to any one of Embodiments 91    to 98, wherein

Q represents the group represented by Q2;

B¹ represents a CH;

B² represents a CR¹;

B³ represents a CH; and

R¹ represents a C1-C2 perfluoroalkyl group.

Next, processes for preparing the Present compound X are described.

Process 1

A compound represented by formula (I-n1) (hereinafter referred to as“Compound (I-n1)”) or a compound represented by formula (I-n2)(hereinafter referred to as “Compound (I-n2)”) may be prepared byreacting a compound represented by formula (I-n0) (hereinafter referredto as “Compound (I-n0)”) with an oxidizing agent. The Compound (I-n2)may also be prepared by reacting the Compound (I-n1) with an oxidizingagent.

[wherein the symbols are the same as defined above.]

First, a method for producing the Compound (I-n1) from the Compound(I-n0) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated hydrocarbons suchas dichloromethane and chloroform (hereinafter collectively referred toas “halogenated hydrocarbons”); nitriles such as acetonitrile(hereinafter collectively referred to as “nitriles”); alcohols such asmethanol and ethanol (hereinafter collectively referred to as“alcohols”); acetic acid; water; and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction includesodium periodate, m-chloroperbenzoic acid (hereinafter referred to as“mCPBA”), and hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, a base or acatalyst may also be used as needed.

Examples of the base include sodium carbonate. When a base is used, thebase is usually used at a ratio of 0.01 to 1 mol, relative to 1 mol ofthe Compound (I-n0).

Examples of the catalyst include tungstic acid and sodium tungstate.When a catalyst is used, the catalyst is usually used at a ratio of 0.01to 0.5 mol, relative to 1 mol of the Compound (I-n0).

In the reaction, the oxidizing agent is usually used at a ratio of 1 to1.2 mol, relative to 1 mol of the Compound (I-n0).

The reaction temperature is usually within the range of −20 to 80° C.The reaction time is usually within the range of 0.1 to 12 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and washing theresulting organic layer with an aqueous solution of a reducing agent(for example, sodium sulfite or sodium thiosulfate) and an aqueoussolution of a base (for example, sodium hydrogen carbonate) as needed.The resulting organic layer may be dried or concentrated to give theCompound (I-n1).

Next, a method for producing the Compound (I-n2) from the Compound(I-n1) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated hydrocarbons,nitriles, alcohols, acetic acid, water, and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction include mCPBAand hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, a base or acatalyst may also be used as needed.

Examples of the base include sodium carbonate. When a base is used, thebase is usually used at a ratio of 0.01 to 1 mol, relative to 1 mol ofthe Compound (I-n1).

Examples of the catalyst include sodium tungstate. When a catalyst isused, the catalyst is usually used at a ratio of 0.01 to 0.5 mol,relative to 1 mol of the Compound (I-n1).

In the reaction, the oxidizing agent is usually used at a ratio of 1 to2 mol, relative to 1 mol of the Compound (I-n1).

The reaction temperature is usually within the range of −20 to 120° C.The reaction time is usually within the range of 0.1 to 12 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and washing theresulting organic layer with an aqueous solution of a reducing agent(for example, sodium sulfite or sodium thiosulfate) and an aqueoussolution of a base (for example, sodium hydrogen carbonate) as needed.The resulting organic layer may be dried or concentrated to give theCompound (I-n2).

Also, the Compound (I-n2) may be prepared in one step reaction (one-pot)by reacting the Compound (I-n0) with an oxidizing agent.

The reaction may be carried out according to the same method as themethod for producing the Compound (I-n2) from the Compound (I-n1) byusually using the oxidizing agent at a ratio of 2 to 5 mol relative to 1mol of the Compound (I-n0).

Process 2

The Compound (I-n0) may be prepared by reacting a compound representedby formula (M-1) (hereinafter referred to as “Compound (M-1)¹”) with acompound represented by formula (R-1) (hereinafter referred to as“Compound (R-1)¹”) in the presence of a base.

[wherein X^(a) represents a fluorine atom, a chlorine atom, or a bromineatom; and the other symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers such astetrahydrofuran (hereinafter referred to as “THF”), 1,2-dimethoxyethane(hereinafter referred to as “DME”), and methyl tert-butyl ether(hereinafter collectively referred to as “ethers”); aromatichydrocarbons such as toluene and xylene (hereinafter collectivelyreferred to as “aromatic hydrocarbons”); nitriles; aprotic polarsolvents such as dimethylformamide (hereinafter referred to as “DMF”),N-methylpyrrolidone (hereinafter referred to as “NMP”), and dimethylsulfoxide (hereinafter referred to as “DMSO”) (hereinafter collectivelyreferred to as “aprotic polar solvents”); water; and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates such as sodium carbonate and potassium carbonate (hereinaftercollectively referred to as “alkali metal carbonates”); alkali metalhydrides such as sodium hydride (hereinafter collectively referred to as“alkali metal hydrides”); and organic bases such as triethylamine,diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine(hereinafter collectively referred to as “organic bases”).

In the reaction, the Compound (R-1) is usually used at a ratio of 1 to 3mol, and the base is usually used at a ratio of 1 to 3 mol, relative to1 mol of the Compound (M-1).

The reaction temperature is usually within the range of −20° C. to 150°C. The reaction time is usually within the range of 0.5 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (I-n0).

The Compound (R-1) is a commercially available compound or may beprepared by using known method(s).

Process 3

A compound represented by formula (P2) (hereinafter referred to as“Compound (P2)”) may be prepared by reacting a compound represented byformula (P1) (hereinafter referred to as “Compound (P1)”) with asulfating agent.

[wherein the symbols are the same as defined above.]

The reaction is carried out in a solvent or in the absence of a solvent.Examples of the solvent include ethers; halogenated hydrocarbons;aromatic hydrocarbons; nitriles; nitrogen-containing aromatic compoundssuch as pyridine, picoline, lutidine, and quinoline; and mixed solventsthereof.

Examples of the sulfating agent to be used in the reaction includephosphorus pentasulfide and Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide).

In the reaction, the sulfating agent is usually used at a ratio of 1 to3 mol, relative to 1 mol of the Compound (P1).

The reaction temperature is usually within the range of 0° C. to 200° C.The reaction time is usually within the range of 1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (P2).

Process 4

A compound represented by formula (P4) (hereinafter referred to as“Compound (P4)¹”) may be prepared by reacting a compound represented byformula (P3) (hereinafter referred to as “Compound (P3)”) with asulfating agent.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 3.

Process 5

The Compound (P1) may be prepared by reacting a compound represented byformula (M-2) (hereinafter referred to as “Compound (M-2)¹”) with acompound represented by formula (M-3) (hereinafter referred to as“Compound (M-3)¹”) in the presence of a base.

[wherein X^(b) represents a halogen atom; and the other symbols are thesame as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include organic bases,alkali metal carbonates, and alkali metal hydrides.

The reaction may also be carried out by using a metal catalyst asneeded. Examples of the metal catalyst include copper catalysts such ascopper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I)oxide, copper(I) trifluoromethanesulfonate benzene complex,tetrakis(acetonitrile)copper(I) hexafluorophosphate, and copper(I)2-thiophenecarboxylate; nickel catalysts such asbis(cyclooctadiene)nickel(0) and nickel(II) chloride; and palladiumcatalysts such as palladium(II) acetate,tetrakis(triphenylphosphine)palladium(0), andtris(dibenzylideneacetone)dipalladium(II) When a metal catalyst is usedin the reaction, the metal catalyst is usually used at a ratio of 0.01to 0.5 mol, relative to 1 mol of the Compound (M-2).

The reaction may also be carried out by using a ligand as needed.Examples of the ligand include triphenylphosphine, Xantphos,2,2′-bis(diphenylphosphino)-1,1′-binaphthyl,1,1′-bis(diphenylphosphino)ferrocene,2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl,2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl,1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol,8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine,trans-N,N′-dimethylcyclohexane-1,2-diamine, andN,N′-dimethylethylenediamine. When a ligand is used in the reaction, theligand is usually used at a ratio of 0.01 to 0.5 mol, relative to 1 molof the Compound (M-2).

In the reaction, the Compound (M-3) is usually used at a ratio of 0.8 to1.2 mol, and the base is usually used at a ratio of 1 to 3 mol, relativeto 1 mol of the Compound (M-2).

The reaction temperature is usually within the range of −20° C. to 150°C. The reaction time is usually within the range of 0.5 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (P1).

Process 6

The Compound (P3) may be prepared by reacting a compound represented byformula (M-4) (hereinafter referred to as “Compound (M-4)”) with theCompound (M-3) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 5.

Process 7

A compound represented by formula (P5) (hereinafter referred to as“Compound (P5)”) may be prepared by reacting a compound represented byformula (M-5) (hereinafter referred to as “Compound (M-5)”) with acompound represented by formula (R-2) (hereinafter referred to as“Compound (R-2)¹”).

[wherein X° represents a chlorine atom, a bromine atom, or an iodineatom; and the other symbols are the same as defined above.]

The reaction is carried out in a solvent or in the absence of a solvent.Examples of the solvent include ethers, aromatic hydrocarbons,halogenated hydrocarbons, esters such as ethyl acetate (hereinaftercollectively referred to as “esters”), nitriles, aprotic polar solvents,and mixed solvents thereof.

The reaction may also be carried out by using a base as needed. Examplesof the base include alkali metal carbonates; and alkali metal hydrogencarbonates such as sodium hydrogen carbonate. When a base is used in thereaction, the base is usually used at a ratio of 1 to 3 mol, relative to1 mol of the Compound (M-5).

In the reaction, the Compound (R-2) is usually used at a ratio of 1 to 3mol, relative to 1 mol of the Compound (M-5).

The reaction temperature is usually within the range of 20 to 200° C.The reaction time is usually within the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (P5).

The Compound (R-2) is a commercially available compound or may beprepared by using known method(s).

Process 8

A compound represented by formula (P6) (hereinafter referred to as“Compound (P6)”) may be prepared by reacting a compound represented byformula (M-6) (hereinafter referred to as “Compound (M-6)”) with acompound represented by formula (R-3) (hereinafter referred to as“Compound (R-3)”).

[wherein the symbols are the same as defined above.]

The reaction is carried out in a solvent or in the absence of a solvent.Examples of the solvent include ethers, aromatic hydrocarbons,halogenated hydrocarbons, esters, nitriles, aprotic polar solvents, andmixed solvents thereof.

In the reaction, the Compound (R-3) is usually used at a ratio of 1 to 3mol, relative to 1 mol of the Compound (M-6).

The reaction temperature is usually within the range of 20 to 200° C.The reaction time is usually within the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (P6).

The Compound (R-3) is a commercially available compound or may beprepared by using known method(s).

Process 9

A compound represented by formula (P7) (hereinafter referred to as“Compound (P7)”) may be prepared by reacting a compound represented byformula (M-7) (hereinafter referred to as “Compound (M-7)”) with acompound represented by formula (R-4) (hereinafter referred to as“Compound (R-4)”).

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 7 by using the Compound (M-7) instead of the Compound (M-5) andusing the Compound (R-4) instead of the Compound (R-2).

The Compound (R-4) is a commercially available compound or may beprepared by using known method(s).

Process 10

An N-oxide compound of the compound represented by formula (I) may beprepared by reacting the compound represented by formula (I) with anoxidizing agent. The reaction may be carried out according to the samemethod as described in, for example, the Process 1, US PatentApplication Publication No. 2018/0009778, or WO 2016/121970 pamphlet.

Process 11

A compound represented by formula (I-n2-NO) may be prepared by reactinga compound represented by formula (I-n2-N) with an oxidizing agent.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 1 or Process 10.

Hereinafter, processes for preparing the production intermediatecompounds are described.

Reference Process 1

A compound represented by formula (M-1-Q1) (hereinafter referred to as“Compound (M-1-Q1)¹”) may be prepared by reacting the Compound (M-2)with a compound represented by formula (M-8) (hereinafter referred to as“Compound (M-8)¹”) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 5.

The Compound (M-8) is a commercially available compound or may beprepared by using known method(s).

Reference Process 2

A compound represented by formula (M-1-Q2) (hereinafter referred to as“Compound (M-1-Q2)¹”) may be prepared by reacting the Compound (M-4)with the Compound (M-8) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 5.

Reference Process 3

A compound represented by formula (M-3-n0) (hereinafter referred to as“Compound (M-3-n0)”) may be prepared by reacting a compound representedby formula (M-8-1) (hereinafter referred to as “Compound (M-8-1)¹”) withthe Compound (R-1) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction may be carried out according to the same method as theProcess 2.

Reference Process 4

A compound represented by formula (M-3-n1) (hereinafter referred to as“Compound (M-3-n1)”) or a compound represented by formula (M-3-n2)(hereinafter referred to as “Compound (M-3-n2)¹”) may be prepared byreacting the Compound (M-3-n0) with an oxidizing agent. The Compound(M-3-n2) may also be prepared by reacting the Compound (M-3-n1) with anoxidizing agent.

[wherein the symbols are the same as defined above.]

These reactions may be carried out according to the same method as theProcess 1.

Reference Process 5

A compound represented by formula (M-2-1) (hereinafter referred to as“Compound (M-2-1)¹”) may be prepared according to the following scheme.

[wherein R⁵⁰ represents a benzyl group or a C1-C3 alkyl group; and theother symbols are the same as defined above.]

A compound represented by formula (M-12) (hereinafter referred to as“Compound (M-12)¹”) may be prepared according to the Process 7 by usinga compound represented by formula (M-9) (hereinafter referred to as“Compound (M-9)”) instead of the Compound (M-5).

A compound represented by formula (M-13) (hereinafter referred to as“Compound (M-13)¹”) may be prepared according to the Process 7 by usinga compound represented by formula (M-10) (hereinafter referred to as“Compound (M-10)”) instead of the Compound (M-5).

The Compound (M-13) may also be prepared according to the Process 2 byusing the Compound (M-12) instead of the Compound (M-1) and using acompound represented by formula (R-5) (hereinafter referred to as“Compound (R-5)”) instead of the Compound (R-1).

The Compound (R-5) is a commercially available compound or may beprepared by using known method(s).

The Compound (M-2-1) may be prepared according to the Process 7 by usinga compound represented by formula (M-11) (hereinafter referred to as“Compound (M-11)”) instead of the Compound (M-5).

The Compound (M-2-1) may also be prepared by reacting the Compound(M-13) wherein R⁵⁰ represents a benzyl group (hereinafter referred to as“Compound (M-13-1)”) with hydrogen in the presence of a catalyst.

The reaction is carried out usually under hydrogen atmosphere of 1 to100 atm and usually in a solvent. Examples of the solvent to be used inthe reaction include ethers, esters, alcohols, water, and mixed solventsthereof.

Examples of the catalyst to be used in the reaction include transitionmetal compounds such as palladium carbon, palladium(II) hydroxide, Raneynickel, and platinum oxide.

In the reaction, the catalyst is usually used at a ratio of 0.001 to 0.5mol, relative to 1 mol of the Compound (M-13-1).

The reaction may also be carried out by using an acid, a base, or thelike as needed.

Examples of the acid include acetic acid and hydrochloric acid, andexamples of the base include tertiary amines such as triethylamine. Whenan acid is used in the reaction, the acid is usually used at a ratio of0.001 to 0.5 mol, relative to 1 mol of the Compound (M-13-1). When abase is used in the reaction, the base is usually used at a ratio of 0.1to 5 mol, relative to 1 mol of the Compound (M-13-1).

The reaction temperature is usually within the range of −20 to 100° C.The reaction time is usually within the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as filtering it, and as needed, extracting it withorganic solvent(s), and drying or concentrating the resulting organiclayer to give the Compound (M-2-1).

Also, the Compound (M-2-1) may also be prepared by reacting the Compound(M-13) with an acid.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated hydrocarbons,water, and mixed solvents thereof.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid and sulfuric acid.

In the reaction, the acid is usually used at a ratio of 1 to 100 mol,relative to 1 mol of the Compound (M-13). The reaction temperature isusually within the range of 50 to 150° C. The reaction time is usuallywithin the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (M-2-1).

The Compound (M-2-1) may also be prepared by hydrolyzing the Compound(M-12) in the presence of an acid or a base.

When the Compound (M-12) is hydrolyzed in the presence of an acid, thereaction is usually carried out in water. Further, ethers, alcohols, orthe like may also be added thereto as a solvent.

Examples of the acid include mineral acids such as hydrochloric acid andsulfuric acid.

In the reaction, the acid is usually used at a ratio of 1 to 100 mol,relative to 1 mol of the Compound (M-12). The reaction temperature isusually within the range of 50 to 100° C. The reaction time is usuallywithin the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (M-2-1).

When the Compound (M-12) is hydrolyzed in the presence of a base, thereaction is usually carried out in water. Further, ethers, alcohols, orthe like may also be added thereto as a solvent.

Examples of the base include alkali metal hydroxides such as sodiumhydroxide and potassium hydroxide.

In the reaction, the base is usually used at a ratio of 1 to 10 mol,relative to 1 mol of the Compound (M-12).

The reaction temperature is usually within the range of 50 to 120° C.The reaction time is usually within the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding an acid thereto to acidify the mixture, thenextracting the resulting mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (M-2-1).

The Compound (M-9), the Compound (M-10), and the Compound (M-11) arecommercially available compounds or may be prepared by using knownmethod(s).

Reference Process 6

A compound represented by formula (M-2-2) (hereinafter referred to as“Compound (M-2-2)”) may be prepared according to the following scheme.

[wherein the symbols are the same as defined above.]

A compound represented by formula (M-17) (hereinafter referred to as“Compound (M-17)”) may be prepared according to the same method asdescribed in the Process 8 by using a compound represented by formula(M-14) (hereinafter referred to as “Compound (M-14)”) instead of theCompound (M-6).

A compound represented by formula (M-18) (hereinafter referred to as“Compound (M-18)”) may be prepared according to the Process 8 by using acompound represented by formula (M-15) (hereinafter referred to as“Compound (M-15)¹”) instead of the Compound (M-6).

Also, the Compound (M-18) may also be prepared according to the Process2 by using the Compound (M-17) instead of the Compound (M-1) and usingthe Compound (R-5) instead of the Compound (R-1).

The Compound (M-2-2) may be prepared according to the Process 8 by usinga compound represented by formula (M-16) (hereinafter referred to as“Compound (M-16)”) instead of the Compound (M-6).

The Compound (M-2-2) may also be prepared according to the method forproducing the Compound (M-2-1) from the Compound (M-13) in the Referenceprocess 5 by using the Compound (M-18) instead of the Compound (M-13).

The Compound (M-2-2) may also be prepared according to the method forproducing the Compound (M-2-1) from the Compound (M-12) in the Referenceprocess 5 by using the Compound (M-17) instead of the Compound (M-12).

The Compound (M-14), the Compound (M-15), and the Compound (M-16) arecommercially available compounds or may be prepared by using knownmethod(s).

Reference Process 7

A compound represented by formula (M-4-1) (hereinafter referred to as“Compound (M-4-1)”) may be prepared according to the following scheme.

[wherein the symbols are the same as defined above.]

A compound represented by formula (M-22) (hereinafter referred to as“Compound (M-22)”) may be prepared according to the Process 7 by using acompound represented by formula (M-19) (hereinafter referred to as“Compound (M-19)¹”) instead of the Compound (M-5) and using the Compound(R-4) instead of the Compound (R-2).

A compound represented by formula (M-23) (hereinafter referred to as“Compound (M-23)”) may be prepared according to the Process 7 by using acompound represented by formula (M-20) (hereinafter referred to as“Compound (M-20)¹”) instead of the Compound (M-5) and using the Compound(R-4) instead of the Compound (R-2).

The Compound (M-23) may also be prepared according to the Process 2 byusing the Compound (M-22) instead of the Compound (M-1) and using theCompound (R-5) instead of the Compound (R-1).

The Compound (M-4-1) may be prepared according to the Process 7 by usinga compound represented by formula (M-21) (hereinafter referred to as“Compound (M-21)”) instead of the Compound (M-5) and using the Compound(R-4) instead of the Compound (R-2).

The Compound (M-4-1) may also be prepared according to the method forproducing the Compound (M-2-1) from the Compound (M-13) in the Referenceprocess 5 by using the Compound (M-23) instead of the Compound (M-13).

The Compound (M-4-1) may also be prepared according to the method forproducing the Compound (M-2-1) from the Compound (M-12) in the Referenceprocess 5 by using the Compound (M-22) instead of the Compound (M-12).

The Compound (M-19), the Compound (M-20), and the Compound (M-21) arecommercially available compounds or may be prepared by using knownmethod(s).

Reference Process 8

A compound represented by formula (M-28) (hereinafter referred to as“Compound (M-28)¹”) may be prepared according to the following scheme.

[wherein R⁵¹ represents an amino group or a hydrazinyl group; and theother symbols are the same as defined above.]

A compound represented by formula (M-25) (hereinafter referred to as“Compound (M-25)”) may be prepared according to the Process 5 by usingthe Compound (M-24) instead of the Compound (M-2).

A compound represented by formula (M-26) (hereinafter referred to as“Compound (M-26)”) may be prepared according to the method for producingthe Compound (M-2-1) from the Compound (M-13) in the Reference process 5by using the Compound (M-25) instead of the Compound (M-13).

A compound represented by formula (M-27) (hereinafter referred to as“Compound (M-27)”) may be prepared by reacting the Compound (M-26) witha chlorinating agent.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, halogenated hydrocarbons, and mixed solvents thereof.

Examples of the chlorinating agent to be used in the reaction includethionyl chloride, oxalyl chloride, phosphorus oxychloride, andphosphorus pentachloride.

In the reaction, the chlorinating agent is usually used at a ratio of 1to 5 mol, relative to 1 mol of the Compound (M-26).

The reaction temperature is usually within the range of 0 to 100° C. Thereaction time is usually within the range of 0.1 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (M-27).

The Compound (M-28) may be prepared by reacting the Compound (M-27) withammonia or hydrazine.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, water, and mixedsolvents thereof.

The reaction may also be carried out by using a base as needed. Examplesof the base include alkali metal hydrides; alkali metal carbonates;tertiary amines such as triethylamine and N,N-diisopropylethylamine; andnitrogen-containing aromatic compounds such as pyridine and4-dimethylaminopyridine. When a base is used in the reaction, the baseis usually used at a ratio of 1 to 10 mol, relative to 1 mol of theCompound (M-27).

In the reaction, ammonia or hydrazine is usually used at a ratio of 1 to10 mol, relative to 1 mol of the Compound (M-27).

The reaction temperature is usually within the range of 0 to 150° C. Thereaction time is usually within the range of 0.5 to 24 hour(s).

When the reaction is completed, the reaction mixture may be subjected toa work-up such as adding water to the reaction mixture, extracting theresulting reaction mixture with organic solvent(s), and drying orconcentrating the resulting organic layer to give the Compound (M-28).

The Compound (M-24) is a commercially available compound or may beprepared by using known method(s).

Reference Process 9

The Compound (M-7) may be prepared according to the following scheme.

[wherein the symbols are the same as defined above.]

A compound represented by formula (M-30) (hereinafter referred to as“Compound (M-30)”) may be prepared according to the Process 5 by using acompound represented by formula (M-29) (hereinafter referred to as“Compound (M-29)¹”) instead of the Compound (M-2).

A compound represented by formula (M-31) (hereinafter referred to as“Compound (M-31)”) may be prepared according to the method for producingthe Compound (M-2-1) from the Compound (M-13) in the Reference process 5by using the Compound (M-30) instead of the Compound (M-13).

A compound represented by formula (M-32) (hereinafter referred to as“Compound (M-32)¹”) may be prepared according to the method forproducing the Compound (M-27) from the Compound (M-26) in the Referenceprocess 8 by using the Compound (M-31) instead of the Compound (M-26).

The Compound (M-7) may be prepared according to the method for producingthe Compound (M-28) from the Compound (M-27) in the Reference process 8by using the Compound (M-32) instead of the Compound (M-27).

The Compound (M-29) is a commercially available compound or may beprepared by using known method(s).

The Present compound or the Present compound X may be mixed with or usedin combination with one or more ingredient(s) selected from the groupconsisting of the following Group (a), Group (b), Group (c), Group (d),Group (e), Group (f), Group (g), and Group (h) (hereinafter referred toas “Present ingredient”).

When the Present compound or the Present compound X is mixed with orused in combination with the Present ingredient, they are usedsimultaneously, separately, or at time intervals with each other.

When the Present compound or the Present compound X is usedsimultaneously with the Present ingredient, the Present compound or thePresent compound X and the Present ingredient may be contained inseparate formulations or contained in one formulation.

One aspect of the present invention provides a composition comprisingone or more ingredient(s) selected from the group consisting of Group(a) and Group (b), and the Present compound.

One aspect of the present invention provides a composition comprisingone or more ingredient(s) selected from the group consisting of Group(a) and Group (b), and the Present compound X (hereinafter referred toas “Composition A”).

Group (a) is a group consisting of each active ingredient ofacetylcholinesterase inhibitors (for example, carbamate insecticides andorganophosphorus insecticides), GABAergic chloride channel antagonists(for example, phenylpyrazole insecticides), sodium channel modulators(for example, pyrethroid insecticides), nicotinic acetylcholine receptorcompetitive modulators (for example, neonicotinoid insecticides),nicotinic acetylcholine receptor allosteric modulators, glutamatergicchloride channel allosteric modulators (for example, macrolideinsecticides), juvenile hormone mimics, multisite inhibitors,chordotonal organ TRPV channel modulators, mites growth inhibitors,mitochondrial ATP biosynthetic enzyme inhibitors, oxidativephosphorylation uncouplers, nicotinic acetylcholine receptor channelblockers (for example, nereistoxin insecticides), chitin synthesisinhibitors, molting inhibitors, ecdysone receptor agonists, octopaminereceptor agonists, mitochondrial electron transport system complex I,II, III, and IV inhibitors, voltage-dependent sodium channel blockers,acetyl CoA carboxylase inhibitors, ryanodine receptor modulators (forexample, diamide insecticides), chordotonal organmodulators, andmicrobial insecticides, and other insecticidal active ingredients,miticidal active ingredients, and nematicidal active ingredients. Theseingredients are described in the classification on the basis of actionmechanism by IRAC.

Group (b) is a group consisting of nucleic acid synthesis inhibitors(for example, phenylamide fungicides and acylamino acid fungicides),cell division and cytoskeleton inhibitors (for example, MBC fungicides),respiration inhibitors (for example, QoI fungicides and QiI fungicides),amino acid synthesis and protein synthesis inhibitors (for example,anilinopyridine fungicides), signaling inhibitors, lipid synthesis andmembrane synthesis inhibitors, sterol biosynthesis inhibitors (forexample, DMI fungicides such as triazole fungicides), cell-wallsynthesis inhibitors, melanin synthesis inhibitors, plant defenseinducers, fungicides with multi-site contact activity, microbialfungicides, and other fungicidal active ingredients. These ingredientsare described in the classification on the basis of action mechanism byFRAC.

Group (c) is a group of plant growth regulatory ingredients (includingmycorrhizal fungi and root nodule bacteria).

Group (d) is a group of phytotoxicity-reducing ingredients.

Group (e) is a group of synergists.

Group (f) is a group of repellent ingredients consisting of birdrepellent ingredients, insect repellent ingredients, and animalrepellent ingredients.

Group (g) is a group of molluscicidal ingredients.

Group (h) is a group of insect pheromones.

Hereinafter, examples of the combination of the Present ingredient andthe Present compound X are described. For example, alanycarb+SXindicates a combination of alanycarb and SX.

The abbreviation of “SX” indicates any one of the Present compounds Xselected from the Compound groups SX1 to SX110 described in Examples.Also, all of the following Present ingredients are known ingredients,and may be obtained from commercially available formulations, or may beprepared by known methods. When the Present ingredient is amicroorganism, it may also be available from a bacterial authoritydepository. Further, the number in parentheses represents the CAS RN(registered trademark).

Combination of the Present ingredient in the above Group (a) and thePresent compound X:

abamectin+SX, acephate+SX, acequinocyl+SX, acetamiprid+SX,acrinathrin+SX, acynonapyr+SX, afidopyropen+SX, afoxolaner+SX,alanycarb+SX, aldicarb+SX, allethrin+SX, alpha-cypermethrin+SX,alpha-endosulfan+SX, aluminium phosphide+SX, amitraz+SX,azadirachtin+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX,azocyclotin+SX, bark of Celastrus angulatus+SX, bendiocarb+SX,benfluthrin+SX, benfuracarb+SX, bensultap+SX, benzoximate+SX,benzpyrimoxan+SX, beta-cyfluthrin+SX, beta-cypermethrin+SX,bifenazate+SX, bifenthrin+SX, bioallethrin+SX, bioresmethrin+SX,bistrifluron+SX, borax+SX, boric acid+SX, broflanilide+SX,bromopropylate+SX, buprofezin+SX, butocarboxim+SX, butoxycarboxim+SX,cadusafos+SX, calcium cyanide+SX, calcium phosphide+SX, carbaryl+SX,carbofuran+SX, carbosulfan+SX, cartap hydrochloride+SX, cartap+SX,chinomethionat+SX, chlorantraniliprole+SX, chlordane+SX,chlorethoxyfos+SX, chlorfenapyr+SX, chlorfenvinphos+SX,chlorfluazuron+SX, chlormephos+SX, chloropicrin+SX, chlorpyrifos+SX,chlorpyrifos-methyl+SX, chromafenozide+SX, clofentezine+SX,clothianidin+SX, coumaphos+SX, cryolite+SX, cyanophos+SX,cyantraniliprole+SX, cycloniliprole+SX, cycloprothrin+SX,cycloxaprid+SX, cyenopyrafen+SX, cyflumetofen+SX, cyfluthrin+SX,cyhalodiamide+SX, cyhalothrin+SX, cyhexatin+SX, cypermethrin+SX,cyphenothrin+SX, cyromazine+SX, dazomet+SX, deltamethrin+SX,demeton-S-methyl+SX, diafenthiuron+SX, diazinon+SX, dichlorvos+SX,dicloromezotiaz+SX, dicofol+SX, dicrotophos+SX, diflovidazin+SX,diflubenzuron+SX, dimefluthrin+SX, dimethoate+SX, dimethylvinphos+SX,dinotefuran+SX, disodium octaborate+SX, disulfoton+SX, DNOC(2-methyl-4,6-dinitrophenol)+SX, doramectin+SX, dried leaves ofDryopteris filix-mas+SX, emamectin-benzoate+SX, empenthrin+SX,endosulfan+SX, EPN (O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX,epsilon-metofluthrin+SX, epsilon-momfluorothrin+SX, esfenvalerate+SX,ethiofencarb+SX, ethion+SX, ethiprole+SX, ethoprophos+SX, etofenprox+SX,etoxazole+SX, extract of Artemisia absinthium+SX, extract of Cassianigricans+SX, extract of Clitoria ternatea+SX, extract of Symphytumofficinale+SX, extracts or simulated blend of Chenopodiumambrosioides+SX, extract of Tanacetum vulgare+SX, extract of Urticadioica+SX, extract of Viscum album+SX, famphur+SX, fenamiphos+SX,fenazaquin+SX, fenbutatin oxide+SX, fenitrothion+SX, fenobucarb+SX,fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX,fenvalerate+SX, fipronil+SX, flometoquin+SX, flonicamid+SX,fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX,flucycloxuron+SX, flucythrinate+SX, fluensulfone+SX, flufenoprox+SX,flufenoxuron+SX, flufiprole+SX, flumethrin+SX, flupyradifurone+SX,flupyrimin+SX, fluralaner+SX, fluvalinate+SX, fluxametamide+SX,formetanate+SX, fosthiazate+SX, furamethrin+SX, furathiocarb+SX,gamma-cyhalothrin+SX, GS-omega/kappa HXTX-Hvla peptide+SX,halfenprox+SX, halofenozide+SX, heptafluthrin+SX, heptenophos+SX,hexaflumuron+SX, hexythiazox+SX, potassium salt of hop beta acid+SX,hydramethylnon+SX, hydroprene+SX, imicyafos+SX, imidacloprid+SX,imiprothrin+SX, indoxacarb+SX, isofenphos+SX, isoprocarb+SX,isopropyl-O-(methoxyaminothiophosphoryl)salicylate+SX, isoxathion+SX,ivermectin+SX, kadethrin+SX, kappa-tefluthrin+SX, kappa-bifenthrin+SX,kinoprene+SX, lambda-cyhalothrin+SX, lepimectin+SX, lime sulfur+SX,lufenuron+SX, machine oil+SX, malathion+SX, mecarbam+SX,meperfluthrin+SX, metaflumizone+SX, metam+SX, methamidophos+SX,methidathion+SX, methiocarb+SX, methomyl+SX, methoprene+SX,methoxychlor+SX, methoxyfenozide+SX, methylbromide+SX, metofluthrin+SX,metolcarb+SX, metoxadiazone+SX, mevinphos+SX, milbemectin+SX, milbemycinoxime+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX,neem oil+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX,novaluron+SX, noviflumuron+SX, oil of the seeds of Chenopodiumanthelminticum+SX, omethoate+SX, oxamyl+SX, oxazosulfyl+SX,oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, permethrin+SX,phenothrin+SX, phenthoate+SX, phorate+SX, phosalone+SX, phosmet+SX,phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX,pirimiphos-methyl+SX, potassium cyanide+SX, prallethrin+SX,profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX,propoxur+SX, propylene glycol alginate+SX, prothiofos+SX,pyflubumide+SX, pymetrozine+SX, pyraclofos+SX, pyrethrins+SX,pyridaben+SX, pyridalyl+SX, pyridaphenthion+SX, pyrifluquinazone+SX,pyrimidifen+SX, pyriminostrobin+SX, pyriprole+SX, pyriproxyfen+SX,quinalphos+SX, resmethrin+SX, rotenone+SX, ryanodine+SX, selamectin+SX,sigma-cypermethrin+SX, silafluofen+SX, sodium borate+SX, sodiumcyanide+SX, sodium metaborate+SX, spinetoram+SX, spinosad+SX,spirodiclofen+SX, spiromesifen+SX, spiropidion+SX, spirotetramat+SX,sulfluramid+SX, sulfotep+SX, sulfoxaflor+SX, sulfur+SX, sulfurylfluoride+SX, tartar emetic+SX, tau-fluvalinate+SX, tebufenozide+SX,tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX,temephos+SX, terbufos+SX, terpene constituents of the extract ofChenopodium ambrosioides near ambrosioides (Brand name: Terpenoid blendQRD 460)+SX, tetrachlorvinphos+SX, tetradifon+SX, tetramethrin+SX,tetramethylfluthrin+SX, tetraniliprole+SX, theta-cypermethrin+SX,thiacloprid+SX, thiamethoxam+SX, thiocyclam+SX, thiodicarb+SX,thiofanox+SX, thiometon+SX, thiosultap-disodium+SX,thiosultap-monosodium+SX, tioxazafen+SX, tolfenpyrad+SX,tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX,trichlorfon+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX,tyclopyrazoflor+SX, vamidothion+SX, wood extract of Quassia amara+SX,XMC (3,5-dimethylphenyl N-methylcarbamate)+SX, xylylcarb+SX,zeta-cypermethrin+SX, zinc phosphide+SX,3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide(1104384-14-6)+SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropanesulfinyl)propaneamide(1477923-37-7)+SX,4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide(1241050-20-3)+SX,3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propaneamide(1118626-57-5)+SX,N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-{ethyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide(1429513-53-0)+SX,N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[ethyl(4-cyanobenzoyl)amino]-2-methoxybenzamide(1609007-65-9)+SX,N-[2-bromo-6-difluoromethoxy-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-{methyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide(1630969-78-6)+SX,1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(885026-50-6)+SX, BT crop protein Cry1Ab+SX, BT crop protein Cry1Ac+SX,BT crop protein Cry1Fa+SX, BT crop protein Cry1A.105+SX, BT crop proteinCry2Ab+SX, BT crop protein Vip3A+SX, BT crop protein Cry3A+SX, BT cropprotein Cry3Ab+SX, BT crop protein Cry3Bb+SX, BT crop proteinCry34Abl/Cry35Abl+SX, Adoxophyes orana granulosis virus BV-0001+SX,Anticarsia gemmatalis mNPV+SX, Autographa californica mNPV+SX, Cydiapomonella GV V15+SX, Cydia pomonella GV V22+SX, Cryptophlebia leucotretaGV+SX, Dendrolimus punctatus cypovirus+SX, Helicoverpa armigera NPVBV-0003+SX, Helicoverpa zea NPV+SX, Lymantria dispar NPV+SX, Mamestrabrassicae NPV+SX, Mamestra configurata NPV+SX, Neodiprion abietisNPV+SX, Neodiprion lecontei NPV+SX, Neodiprion sertifer NPV+SX, Nosemalocustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodiainterpunctella GV+SX, Spodoptera exigua mNPV+SX, Spodoptera littoralismNPV+SX, Spodoptera litura NPV+SX, Arthrobotrys dactyloides+SX, Bacillusfirmus GB-126+SX, Bacillus firmus 1-1582+SX, Bacillus megaterium+SX,Bacillus sp. AQ175+SX, Bacillus sp. AQ177+SX, Bacillus sp. AQ178+SX,Bacillus sphaericus 2362+SX, Bacillus sphaericus ABTS1743+SX, Bacillussphaericus Serotype H5a5b+SX, Bacillus thuringiensis AQ52+SX, Bacillusthuringiensis BD #32+SX, Bacillus thuringiensis CR-371+SX, Bacillusthuringiensis subsp. Aizawai ABTS-1857+SX, Bacillus thuringiensis subsp.Aizawai AM65-52+SX, Bacillus thuringiensis subsp. Aizawai GC-91+SX,Bacillus thuringiensis subsp. Aizawai Serotype H-7+SX, Bacillusthuringiensis subsp. Kurstaki ABTS351+SX, Bacillus thuringiensis subsp.Kurstaki BMP123+SX, Bacillus thuringiensis subsp. Kurstaki EG234+SX,Bacillus thuringiensis subsp. Kurstaki EG7841+SX, Bacillus thuringiensissubsp. Kurstaki EVB¹¹³-19+SX, Bacillus thuringiensis subsp. KurstakiF810+SX, Bacillus thuringiensis subsp. Kurstaki HD-1+SX, Bacillusthuringiensis subsp. Kurstaki PB54+SX, Bacillus thuringiensis subsp.Kurstaki SA-11+SX, Bacillus thuringiensis subsp. Kurstaki SA-12+SX,Bacillus thuringiensis subsp. Tenebriosis NB176+SX, Bacillusthuringiensis subsp. Thuringiensis MPPL002+SX, Bacillus thuringiensissubsp. morrisoni+SX, Bacillus thuringiensis var. colmeri+SX, Bacillusthuringiensis var. darmstadiensis 24-91+SX, Bacillus thuringiensis var.dendrolimus+SX, Bacillus thuringiensis var. galleriae+SX, Bacillusthuringiensis var. israelensis BMP144+SX, Bacillus thuringiensis var.israelensis serotype H-14+SX, Bacillus thuringiensis var. japonensisbuibui+SX, Bacillus thuringiensis var. san diego M-7+SX, Bacillusthuringiensis var. 7216+SX, Bacillus thuringiensis var. aegypti+SX,Bacillus thuringiensis var. T36+SX, Beauveria bassiana ANT-03+SX,Beauveria bassiana ATCC74040+SX, Beauveria bassiana GHA+SX, Beauveriabrongniartii+SX, Burkholderia rinojensis A396+SX, Chromobacteriumsubtsugae PRAA⁴-1T+SX, Dactyllela ellipsospora+SX, Dectylariathaumasia+SX, Hirsutella minnesotensis+SX, Hirsutella rhossiliensis+SX,Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium lecaniiKV01+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX,Lecanicillium lecanii conidia of strain DAOM216596+SX, Metarhiziumanisopliae F52+SX, Metarhizium anisopliae var. acridum+SX, Metarhiziumflavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomycesfumosoroseus Apopka97+SX, Paecilomyces lilacinus 251+SX, Paecilomycestenuipes T1+SX, Paenibacillus popilliae+SX, Pasteuria nishizawae Pn1+SX,Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thoynei+SX,Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticilliumlecani NCIM1312+SX, lenoremycin+SX, concanamycin A+SX, acetoprole+SX,lotilaner+SX, sarolaner+SX, isocycloseram+SX, Metarhizium anisopliaevar. anisopliae BIPESCO 5/F52+SX, Lecanicillium muscarium Ve6+SX,N-ethyl-5-methyl-1-(3-methylbutan-2-yl)-N-(pyridazin-4-yl)-1H-pyrazole-4-carboxamide(1403615-77-9)+SX, imidaclothiz+SX.

Combination of the Present ingredient in the above Group (b) and thePresent compound X:

acibenzolar-S-methyl+SX, aldimorph+SX, ametoctradin+SX, aminopyrifen+SX,amisulbrom+SX, anilazine+SX, azaconazole+SX, azoxystrobin+SX, basiccopper sulfate+SX, benalaxyl+SX, benalaxyl-M+SX, benodanil+SX,benomyl+SX, benthiavalicarb+SX, benthivalicarb-isopropyl+SX,benzovindiflupyr+SX, binapacryl+SX, biphenyl+SX, bitertanol+SX,bixafen+SX, blasticidin-S+SX, Bordeaux mixture+SX, boscalid+SX,bromothalonil+SX, bromuconazole+SX, bupirimate+SX, captafol+SX,captan+SX, carbendazim+SX, carboxin+SX, carpropamid+SX,chinomethionat+SX, chitin+SX, chloroneb+SX, chlorothalonil+SX,chlozolinate+SX, colletochlorin B+SX, copper(II) acetate+SX, copper(II)hydroxide+SX, copper oxychloride+SX, copper(II) sulfate+SX,coumoxystrobin+SX, cyazofamid+SX, cyflufenamid+SX, cymoxanil+SX,cyproconazole+SX, cyprodinil+SX, dichlobentiazox+SX, dichlofluanid+SX,diclocymet+SX, diclomezine+SX, dicloran+SX, diethofencarb+SX,difenoconazole+SX, diflumetorim+SX, dimethachlone+SX, dimethirimol+SX,dimethomorph+SX, dimoxystrobin+SX, diniconazole+SX, diniconazole-M+SX,dinocap+SX, dipotassium hydrogenphosphite+SX, dipymetitrone+SX,dithianon+SX, dodecylbenzenesulphonic acid bisethylenediamine copper(II)salt+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX,epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX,etridiazole+SX, extract from Melaleuca alternifolia+SX, extract fromReynoutria sachalinensis+SX, extract from the cotyledons of lupineplantlets (“BLAD”)+SX, extract of Allium sativum+SX, extract ofEquisetum arvense+SX, extract of Tropaeolum majus+SX, famoxadone+SX,fenamidone+SX, fenaminstrobin+SX, fenarimol+SX, fenbuconazole+SX,fenfuram+SX, fenhexamid+SX, fenoxanil+SX, fenpiclonil+SX,fenpicoxamid+SX, fenpropidin+SX, fenpropimorph+SX, fenpyrazamine+SX,fentin acetate+SX, fentin chloride+SX, fentin hydroxide+SX, ferbam+SX,ferimzone+SX, florylpicoxamid+SX, fluazinam+SX, fludioxonil+SX,flufenoxystrobin+SX, fluindapyr+SX, flumorph+SX, fluopicolide+SX,fluopyram+SX, fluopimomide+SX, fluoroimide+SX, fluoxastrobin+SX,fluquinconazole+SX, flusilazole+SX, flusulfamide+SX, flutianil+SX,flutolanil+SX, flutriafol+SX, fluxapyroxad+SX, folpet+SX, fosetyl+SX,fosetyl-aluminium+SX, fuberidazole+SX, furalaxyl+SX, furametpyr+SX,guazatine+SX, hexaconazole+SX, hymexazole+SX, imazalil+SX,imibenconazole+SX, iminoctadine+SX, iminoctadine triacetate+SX,inpyrfluxam+SX, iodocarb+SX, ipconazole+SX, ipfentrifluconazole+SX,ipflufenoquin+SX, iprobenfos+SX, iprodione+SX, iprovalicarb+SX,isofetamid+SX, isoflucypram+SX, isoprothiolane+SX, isopyrazam+SX,isotianil+SX, kasugamycin+SX, kresoxim-methyl+SX, laminarin+SX, leavesand bark of Quercus+SX, mancozeb+SX, mandestrobin+SX, mandipropamid+SX,maneb+SX, mefentrifluconazole+SX, mepanipyrim+SX, mepronil+SX,meptyldinocap+SX, metalaxyl+SX, metalaxyl-M+SX, metconazole+SX,methasulfocarb+SX, metiram+SX, metominostrobin+SX, metrafenone+SX,metyltetraprole+SX, mineral oils+SX, myclobutanil+SX, naftifine+SX,nuarimol+SX, octhilinone+SX, ofurace+SX, orysastrobin+SX, oxadixyl+SX,oxathiapiprolin+SX, oxine-copper+SX, oxolinic acid+SX, oxpoconazole+SX,oxpoconazole fumarate+SX, oxycarboxin+SX, oxytetracycline+SX,pefurazoate+SX, penconazole+SX, pencycuron+SX, penflufen+SX,penthiopyrad+SX, phenamacril+SX, phosphorous acid+SX, phthalide+SX,picarbutrazox+SX, picoxystrobin+SX, piperalin+SX, polyoxins+SX,potassium hydrogencarbonate+SX, potassium dihydrogenphosphite+SX,probenazole+SX, prochloraz+SX, procymidone+SX, propamidine+SX,propamocarb+SX, propiconazole+SX, propineb+SX, proquinazid+SX,prothiocarb+SX, prothioconazole+SX, pydiflumetofen+SX,pyraclostrobin+SX, pyrametostrobin+SX, pyraoxystrobin+SX,pyrapropoyne+SX, pyraziflumid+SX, pyrazophos+SX, pyribencarb+SX,pyributicarb+SX, pyridachlometyl+SX, pyrifenox+SX, pyrimethanil+SX,pyrimorph+SX, pyriofenone+SX, pyrisoxazole+SX, pyroquilon+SX, Quillajaextract+SX, quinconazole+SX, quinofumelin+SX, quinoxyfen+SX,quintozene+SX, Saponins of Chenopodium quinoa+SX, sedaxane+SX,silthiofam+SX, simeconazole+SX, sodium hydrogencarbonate+SX,spiroxamine+SX, streptomycin+SX, sulfur+SX, tebuconazole+SX,tebufloquin+SX, teclofthalam+SX, tecnazene+SX, terbinafine+SX,tetraconazole+SX, thiabendazole+SX, thifluzamide+SX, thiophanate+SX,thiophanate-methyl+SX, thiram+SX, thymol+SX, tiadinil+SX,tolclofos-methyl+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX,triadimefon+SX, triadimenol+SX, triazoxide+SX, triclopyricarb+SX,tricyclazole+SX, tridemorph+SX, trifloxystrobin+SX, triflumizole+SX,triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX,vinclozolin+SX, yellow mustard powder+SX, zinc thiazole+SX, zineb+SX,ziram+SX, zoxamide+SX,3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide(1639015-48-7)+SX,3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide(1639015-49-8)+SX,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(141573-94-6)+SX,3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethylindan-4-yl]-1-methylpyrazole-4-carboxamide(1513466-73-3)+SX,N′-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide(1202781-91-6)+SX,2-{3-[2-(1-{[3,5-bis(difluoromethyl)-TH-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl=methanesulfonate(1360819-11-9)+SX,4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine(1362477-26-6)+SX,2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline(1257056-97-5)+SX,5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidineamine(1174376-25-0)+SX,5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one(1616664-98-2)+SX,N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide(1052688-31-9)+SX,N′-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide(929908-57-6)+SX, ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate(39491-78-6)+SX,N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine(1446247-98-8)+SX,α-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol(1229605-96-2)+SX,(αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol(1229606-46-5)+SX,(αR)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol(1229606-02-3)+SX,2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione(1342260-19-8)+SX,2-{[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione(1638897-70-7)+SX,2-{[(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione(1638897-71-8)+SX,2-{[(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione(1638897-72-9)+SX,2-{[(2S,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione(1638897-73-0)+SX,1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate (1342260-26-7)+SX,1-{[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate (1638897-82-1)+SX,1-{[(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate (1638897-84-3)+SX,1-{[(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate (1638897-86-5)+SX,1-{[(2S,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate (1638897-89-8)+SX,5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1394057-11-4)+SX,(1R,2S,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801930-06-2)+SX,(1S,2R,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801930-07-3)+SX,(1R,2R,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-53-8)+SX,(1S,2S,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-54-9)+SX,(1R,2R,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-55-0)+SX,(1S,2S,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-56-1)+SX,(1R,2S,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-57-2)+SX,(1S,2R,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801919-58-3)+SX,methyl=3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(1791398-02-1)+SX,methyl=(1R,2S,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-90-2)+SX,methyl=(1S,2R,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-91-3)+SX,methyl=(1R,2R,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-92-4)+SX,methyl=(1S,2S,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-93-5)+SX,methyl=(1R,2R,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-94-6)+SX,methyl=(1S,2S,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2080743-95-7)+SX,methyl=(1R,2S,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2081061-22-3)+SX,methyl=(1S,2R,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate(2081061-23-4)+SX,2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1394057-13-6)+SX,(1R,2S,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801930-08-4)+SX,(1S,2R,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1801930-09-5)+SX,(1R,2R,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-08-4)+SX,(1S,2S,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-10-8)+SX,(1R,2R,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-13-1)+SX,(1S,2S,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-16-4)+SX,(1R,2S,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-20-0)+SX,(1S,2R,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(1638898-24-4)+SX,(R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol(1801919-59-4)+SX,(R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol(1616236-94-2)+SX,(R)-1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol(1801919-60-7)+SX,(R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol(1801919-61-8)+SX,3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine(847749-37-5)+SX,Agrobacterium radiobactor K1026+SX, Agrobacterium radiobactor K84+SX,Bacillus amyloliquefaciens AT332+SX, Bacillus amyloliquefaciens B3+SX,Bacillus amyloliquefaciens D747+SX, Bacillus amyloliquefaciens DB101+SX,Bacillus amyloliquefaciens DB102+SX, Bacillus amyloliquefaciens GB03+SX,Bacillus amyloliquefaciens FZB24+SX, Bacillus amyloliquefaciensFZB42+SX, Bacillus amyloliquefaciens IN937a+SX, Bacillusamyloliquefaciens MBI600+SX, Bacillus amyloliquefaciens QST713+SX,Bacillus amyloliquefaciens isolate B246+SX, Bacillus amyloliquefaciensF727+SX, Bacillus licheniformis HB-2+SX, Bacillus licheniformisSB3086+SX, Bacillus pumilus AQ717+SX, Bacillus pumilus BUF-33+SX,Bacillus pumilus GB34+SX, Bacillus pumilus QST2808+SX, Bacillus simplexCGF2856+SX, Bacillus subtilis AQ153+SX, Bacillus subtilis AQ743+SX,Bacillus subtilis BU1814+SX, Bacillus subtilis D747+SX, Bacillussubtilis DB101+SX, Bacillus subtilis FZB24+SX, Bacillus subtilisGB03+SX, Bacillus subtilis HAI0404+SX, Bacillus subtilis IAB/BSO3+SX,Bacillus subtilis MBI600+SX, Bacillus subtilis QST30002/AQ30002+SX,Bacillus subtilis QST30004/AQ30004+SX, Bacillus subtilis QST713+SX,Bacillus subtilis QST714+SX, Bacillus subtilis var. AmyloliquefaciensFZB24+SX, Bacillus subtilis Y1336+SX, Burkholderia cepacia+SX,Burkholderia cepacia type Wisconsin J82+SX, Burkholderia cepacia typeWisconsin M54+SX, Candida oleophila O+SX, Candida saitoana+SX,Chaetomium cupreum+SX, Clonostachys rosea+SX, Coniothyrium minitansCGMCC8325+SX, Coniothyrium minitans CON/M/91-8+SX, Cryptococcusalbidus+SX, Erwinia carotovora subsp. carotovora CGE234M403+SX, Fusariumoxysporum Fo47+SX, Gliocladium catenulatum J1446+SX, Paenibacilluspolymyxa AC-1+SX, Paenibacillus polymyxa BS-0105+SX, Pantoea agglomeransE325+SX, Phlebiopsis gigantea VRA1992+SX, Pseudomonas aureofaciensTX-1+SX, Pseudomonas chlororaphis 63-28+SX, Pseudomonas chlororaphisMA342+SX, Pseudomonas fluorescens 1629RS+SX, Pseudomonas fluorescensA506+SX, Pseudomonas fluorescens CL145A+SX, Pseudomonas fluorescensG7090+SX, Pseudomonas sp. CAB-02+SX, Pseudomonas syringae 742RS+SX,Pseudomonas syringae MA-4+SX, Pseudozyma flocculosa PF-A²²UL+SX,Pseudomonas rhodesiae HAI-0804+SX, Pythium oligandrum DV74+SX,Streptomyces griseoviridis K61+SX, Streptomyces lydicus WYCD108US+SX,Streptomyces lydicus WYEC108+SX, Talaromyces flavus SAY-Y-94-01+SX,Talaromyces flavus V117b+SX, Trichoderma asperellum ICC012+SX,Trichoderma asperellum SKT-1+SX, Trichoderma asperellum T34+SX,Trichoderma atroviride CNCM 1-1237+SX, Trichoderma atroviride LC52+SX,Trichoderma atroviride SC1+SX, Trichoderma atroviride SKT-1+SX,Trichoderma gamsii ICC080+SX, Trichoderma harzianum 21+SX, Trichodermaharzianum DB104+SX, Trichoderma harzianum DSM 14944+SX, Trichodermaharzianum ESALQ-1303+SX, Trichoderma harzianum ESALQ-1306+SX,Trichoderma harzianum IIHR-Th-2+SX, Trichoderma harzianum kd+SX,Trichoderma harzianum MO1+SX, Trichoderma harzianum SF+SX, Trichodermaharzianum T22+SX, Trichoderma harzianum T39+SX, Trichoderma harzianumTH35+SX, Trichoderma polysporum IM1206039+SX, Trichodermastromaticum+SX, Trichoderma virens G-41+SX, Trichoderma virens GL-21+SX,Trichoderma viride+SX, Variovorax paradoxus CGF4526+SX, Harpinprotein+SX, Trichoderma harzianum ITEM908+SX, Trichoderma harzianumT78+SX, methyl({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate(1605879-98-8)+SX,2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide(1616239-21-4)+SX,2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide(1847460-02-9)+SX,2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide(1847460-05-2)+SX,(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide(1445331-27-0)+SX, Bacillus amyloliquefaciens subsp. plantarum D747+SX,Pythium oligandrum M1+SX, Trichoderma asperellum T25+SX, Trichodermaasperellum TV1+SX, Trichoderma atroviride IMI 206040+SX, Trichodermaatroviride T11+SX, Bacillus amyloliquefaciens (Aveo (trademark) EZNematicide)+SX.

Combination of the Present ingredient in the above Group (c) and thePresent compound X:

1-methylcyclopropene+SX, 2,3,5-triiodobenzoic acid+SX, IAA((1H-indol-3-yl)acetic acid)+SX, IBA (4-(1H-indol-3-yl)butyric acid)+SX,MCPA (2-(4-chloro-2-methylphenoxy)acetic acid)+SX, MCPB(4-(4-chloro-2-methylphenoxy)butyric acid)+SX, 4-CPA(4-chlorophenoxyacetic acid)+SX, 5-aminolevulinic acid hydrochloride+SX,6-benzylaminopurine+SX, abscisic acid+SX, AVG(aminoethoxyvinylglycine)+SX, ancymidol+SX, butralin+SX, calciumcarbonate+SX, calcium chloride+SX, calcium formate+SX, calciumperoxide+SX, calcium polysulfide+SX, calcium sulfate+SX,chlormequat-chloride+SX, chlorpropham+SX, choline chloride+SX,cloprop+SX, cyanamide+SX, cyclanilide+SX, daminozide+SX, decan-1-ol+SX,dichlorprop+SX, dikegulac+SX, dimethipin+SX, diquat+SX, ethephon+SX,ethychlozate+SX, flumetralin+SX, flurprimidol+SX, forchlorfenuron+SX,Gibberellin A+SX, Gibberellin A3+SX, inabenfide+SX, Kinetin+SX, maleichydrazide+SX, mefluidide+SX, mepiquat-chloride+SX, oxidizedglutathione+SX, pacrobutrazol+SX, pendimethalin+SX,prohexandione-calcium+SX, prohydrojasmon+SX, pyraflufen-ethyl+SX,sintofen+SX, sodium 1-naphthaleneacetate+SX, sodium cyanate+SX,streptmycin+SX, thidiazuron+SX, triapenthenol+SX, Tribufos+SX,trinexapac-ethyl+SX, uniconazole-P+SX,2-(naphthalen-1-yl)acetamide(2-(naphthalene-1-yl)acetamide)+SX,[4-oxo-4-(2-phenylethyl)amino]butyric acid+SX, methyl5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate+SX,3-[(6-chloro-4-phenylquinazolin-2-yl)amino]-1-propanol+SX,formononetin+SX, Glomus intraradices+SX, Glomus mosseae+SX, Glomusaggregatum+SX, Glomus etunicatum+SX, Bradyrhizobium elkani+SX,Bradyrhizobium japonicum+SX, Bradyrhizobium lupini+SX, Rhizobiumleguminosarum bv. trifolii+SX, Rhizobium leguminosarum bv. phaseoli+SX,Rhizobium leguminosarum bv. viciae+SX, Sinorhizobium meliloti+SX,Rhizobium fredii+SX, Rhizobium loti+SX, Rhizobium trifolii+SX, Rhizobiumtropici+SX, 1,3-diphenylurea+SX, Azorhizobium caulinodans+SX,Azospirillum amazonense+SX, Azospirillum brasilense XOH+SX, Azospirillumbrasilense Ab-V5+SX, Azospirillum brasilense Ab-V6+SX, Azospirillumcaulinodans+SX, Azospirillum halopraeferens+SX, Azospirillumirakense+SX, Azospirillum lipoferum+SX, Bradyrhizobium elkanii SEMIA587+SX, Bradyrhizobium elkanii SEMIA 5019+SX, Bradyrhizobium japonicumTA-11+SX, Bradyrhizobium japonicum USDA 110+SX, Bradyrhizobiumliaoningense+SX, Delftia acidovorans RAY209+SX, Gigaspora margarita+SX,Gigaspora rosea+SX, Glomus deserticola+SX, Glomus monosporum+SX,Mesorhizobium ciceri+SX, Mesorhizobium huakii+SX, Rhizophagus clarus+SX,Rhizobium etli+SX, Rhizobium galegae+SX, Rhizophagus irregularis DAOM197198+SX, Paraglomus brasillianum+SX, Claroideoglomus claroideum+SX,lipochitooligosaccharide SP104+SX, Zucchini Yellow Mosaik Virus weakstrain+SX.

Combination of the Present ingredient in the above Group (d) and thePresent compound X:

allidochlor+SX, benoxacor+SX, cloquintocet+SX, cloquintocet-mexyl+SX,cyometrinil+SX, cyprosulfamide+SX, dichlormid+SX, dicyclonone+SX,dimepiperate+SX, disulfoton+SX, dymron+SX, fenchlorazole+SX,fenchlorazole-ethyl+SX, fenclorim+SX, flurazole+SX, furilazole+SX,fluxofenim+SX, Hexim+SX, isoxadifen+SX, isoxadifen-ethyl+SX,mecoprop+SX, mefenpyr+SX, mefenpyr-ethyl+SX, mefenpyr-diethyl+SX,mephenate+SX, metcamifen+SX, oxabetrinil+SX, 1,8-naphthalicanhydride+SX, 1,8-octamethylene diamine+SX, AD-67(4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane)+SX, CL-304415(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid)+SX, CSB(1-bromo-4-[(chloromethyl) sulfonyl]benzene)+SX, DKA-24(2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-(2-propenyl)acetamide)+SX,MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane)+SX, MG-838 (2-propenyl1-oxa-4-azaspiro[4.5]decane-4-carbodithioate)+SX, PPG-1292(2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide)+SX,R-28725 (3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine)+SX, R-29148(3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine)+SX, TI-35(1-(dichloroacetyl)azepane)+SX.

Combination of the Present ingredient in the above Group (e) and thePresent compound X:

1-dodecyl-1H-imidazole+SX,N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide+SX,bucarpolate+SX, N,N-dibutyl-4-chlorobenzenesulfonamide+SX,dietholate+SX, diethylmaleate+SX, piperonyl butoxide+SX, piperonylcyclonene+SX, piprotal+SX, propyl isome+SX, safroxan+SX, sesamex+SX,sesamolin+SX, sulfoxide+SX, Verbutin+SX, DMC(1,1-bis(4-chlorophenyl)ethanol)+SX, FDMC(1,1-bis(4-chlorophenyl)-2,2,2-trifluoroethanol)+SX, ETN(1,2-epoxy-1,2,3,4-tetrahydronaphthalene)+SX, ETP(1,1,1-trichloro-2,3-expoxypropane)+SX, PSCP (phenylsaligenin cyclicphosphate)+SX, TBPT (S,S,S-tributyl phosphorotrithioate)+SX, TPP(triphenyl phosphate)+SX.

Combination of the Present ingredient in the above Group (f) and thePresent compound X:

anthraquinone+SX, chloralose+SX, acrep+SX, butopyronoxyl+SX, camphor+SX,d-camphor+SX, carboxide+SX, dibutyl phthalate+SX, deet+SX,dimethylcarbate+SX, dimethylphthalate+SX, dibutyl succinate+SX, dibutyladipate+SX, ethohexadiol+SX, hexamide+SX, icaridin+SX,methoquin-butyl+SX, methylneodecanamide+SX, 2-(octylthio)ethanol+SX,butoxypolypropylene glycol+SX, oxamate+SX, quwenzhi+SX, quyingding+SX,zengxiaon+SX, rebemide+SX, copper naphthenate+SX, zinc naphthenate+SX.

Combination of the Present ingredient in the above Group (g) and thePresent compound X:

bis(tributyltin) oxide+SX, allicin+SX, bromoacetamide+SX,cloethocarb+SX, copper sulfate+SX, fentin+SX, ferric phosphate+SX,metaldehyde+SX, niclosamide+SX, pentachlorophenol+SX, sodiumpentachlorophenoxide+SX, tazimcarb+SX, tralopyril+SX, trifenmorph+SX.

Combination of the Present ingredient in the above Group (h) and thePresent compound X:

(E)-2-hexenal+SX, (E)-2-octadecenal+SX, (E)-4-tridecen-1-yl acetate+SX,(E)-5-decen-1-yl acetate+SX, (E)-5-decen-1-ol+SX,(E)-3,3-dimethylcyclohexylideneacetaldehyde+SX, (E)-7-dodecen-1-ylacetate+SX, (E)-8-dodecen-1-yl acetate+SX, (E)-9-dodecen-1-ylacetate+SX, (E)-10-hexadecenal+SX, (E)-11-hexadecen-1-yl acetate+SX,(E)-11-tetradecen-1-yl acetate+SX, (E)-11-tetradecen-1-ol+SX,(E)-4-tridecen-1-yl acetate+SX, (E)-6-methylhept-2-en-4-ol+SX,(Z)-2-(3,3-dimethylcyclohexylidene)ethanol+SX, (Z)-4-decen-1-ylacetate+SX, (Z)-4-tridecen-1-yl acetate+SX, (Z)-5-decen-1-yl acetate+SX,(Z)-5-decen-1-ol+SX, (Z)-7-tetradecenal+SX, (Z)-7-dodecen-1-ylacetate+SX, (Z)-8-dodecen-1-yl acetate+SX, (Z)-9-dodecen-1-ylacetate+SX, (Z)-8-dodecen-1-ol+SX, (Z)-9-hexadecenal+SX,(Z)-10-hexadecen-1-yl acetate+SX, (Z)-11-hexadecen-1-ol+SX,(Z)-11-hexadecenal+SX, (Z)-11-hexadecen-1-yl acetate+SX,(Z)-11-octadecenal+SX, (Z)-13-octadecenal+SX,(Z)-hexadec-13-en-11-yn-1-yl acetate+SX, (Z)-13-octadecenal+SX,(Z)-icos-13-en-10-one+SX, (Z)-7-tetradecenal+SX,(Z)-tetradec-9-en-1-ol+SX, (Z)-9-tetradecen-1-yl acetate+SX,(Z)-11-tetradecen-1-yl acetate+SX, (Z)-13-icosen-10-one+SX,(Z,E)-7,11-hexadecadien-1-yl acetate+SX, (Z,E)-9,12-tetradecadien-1-ylacetate+SX, (E,Z)-4,10-tetradecadien-1-yl acetate+SX,(E,E)-8,10-dodecadien-1-ol+SX, (E,E)-10,12-hexadecadienal+SX,(E,E)-9,11-tetradecadien-1-yl acetate+SX,(E,Z)-2,13-octadecadien-1-ol+SX, (E,Z)-3,13-octadecadien-1-ol+SX,(E,Z)-2,13-octadecadien-1-yl acetate+SX, (E,Z)-3,13-octadecadien-1-ylacetate+SX, (E,Z)-7,9-dodecadien-1-yl acetate+SX,(E,E)-7,9-dodecadien-1-yl acetate+SX, (Z,E)-9,12-tetradecadien-1-ylacetate+SX, (Z,E)-9,11-tetradecadien-1-yl acetate+SX,(Z,E)-7,11-hexadecadien-1-yl acetate+SX,(Z,Z)-3,13-octadecadien-1-ol+SX, (Z,Z)-4,7-decadien-1-yl acetate+SX,(Z,Z)-3,13-octadecadien-1-yl acetate+SX, (Z,Z)-7,11-hexadecadien-1-ylacetate+SX, (Z,Z,E)-7,11,13-hexadecatrienal+SX,(5R)-5-[(1Z)-1-decen-1-yl]dihydro-2(3H)-furanone+SX,(2R,5R)-ethyl-1,6-dioxaspiro[4,4]nonane+SX,(2R,5S)-ethyl-1,6-dioxaspiro[4,4]nonane+SX,(4R,8R)-4,8-dimethyldecanal+SX, (4R,8S)-4,8-dimethyldecanal+SX,2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3,2,1]octane+SX,(−)-4-methyl-3-heptanol+SX, 1,7-dioxaspiro[5,5]undecane+SX, 3-carene+SX,3-methylcyclohex-2-en-1-one+SX, 14-methyloctadec-1-ene+SX,4-methylnonan-5-ol+SX, 4-methylnonan-5-one+SX, 4-(3-oxobutyl)phenylacetate+SX, dodecyl acetate+SX, dodeca-8,10-dien-1-yl acetate+SX, ethyl(2E,4Z)-decadienoate+SX, ethyl 4-methyloctanoate+SX, methyl2,6,10-trimethyldodecanoate+SX, tetradecan-1-ol+SX,tetradec-11-en-1-ol+SX, tetradec-11-en-1-yl acetate+SX, tridec-4-en-1-ylacetate+SX, (3S,6R)-3-methyl-6-isopropenyl-9-decen-1-yl acetate+SX,(3S,6S)-3-methyl-6-isopropenyl-9-decen-1-yl acetate+SX,alpha-multistriatin+SX, alpha-pinene+SX, endo-brevicomin+SX,exo-brevicomin+SX, camphene+SX, codlelure+SX, codlemone+SX, cuelure+SX,disparlure+SX, dominicalure+SX, eugenol+SX, farnesol+SX, ferrolure+SX,frontalin+SX, gossyplure+SX, grandlure+SX, grandlure I+SX, grandlureII+SX, grandlure III+SX, grandlure IV+SX, hexalure+SX, ipsdienol+SX,ipsenol+SX, japonilure+SX, lineatin+SX, litlue+SX, looplure+SX,medlure+SX, megatomoic acid+SX, methyleugenol+SX, muscalure+SX,nerolidol+SX, orfralure+SX, oryctalure+SX, ostramone+SX, rhyncolure+SX,siglure+SX, sordidin+SX, sulcatol+SX, trimedlure+SX, trimedlure A+SX,trimedlure B1+SX, trimedlure B2+SX, trimedlure C+SX, trunc-call+SX,(E)-verbenol+SX, (Z)-verbenol+SX, trans-verbenol+SX, (S)-verbenone+SX.

Examples of the mixture ratio of the Present compound X and the Presentingredient include, but are not limited to,1000:1 to 1:1000, 500:1 to1:500, 100:1 to 1:100, 50:1 to 1:50, 20:1 to 1:20, 10:1 to 1:10, 3:1 to1:3, 1:1 to 1:500, 1:1 to 1:100, 1:1 to 1:50, 1:1 to 1:20, and 1:1 to1:10 in the ratio by weight (Present compound X:Present ingredient)

The Present compounds or the Present compounds X have control effects onharmful arthropods such as harmful insects and harmful mites, harmfulnematodes, and harmful mollusks. Examples of the harmful arthropods,harmful nematodes, and harmful mollusks include the followings.

Hemiptera:

from the family Delphacidae, for example, small brown planthopper(Laodelphax striatellus), brown planthopper (Nilaparvata lugens),white-backed planthopper (Sogatella furcifera), corn planthopper(Peregrinus maidis), cereal leafhopper (Javesella pellucida), sugarcaneleafhopper (Perkinsiella saccharicida), and Tagosodes orizicolus; fromthe family Cicadellidae, for example, green rice leafhopper (Nephotettixcincticeps), green paddy leafhopper (Nephotettix virescens), riceleafhopper (Nephotettix nigropictus), zigzag-striped leafhopper (Reciliadorsalis), tea green leafhopper (Empoasca onukii), potato leafhopper(Empoasca fabae), corn leafhopper (Dalbulus maidis), and rice leafhopper(Cofana spectra);

from the family Cercopidae, for example, Mahanarva posticata andMahanarva fimbriolata;

from the family Aphididae, for example, bean aphid (Aphis fabae),soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), greenapple aphid (Aphis pomi), apple aphid (Aphis spiraecola), green peachaphid (Myzus persicae), leaf-curling plum aphid (Brachycaudushelichrysi), cabbage aphid (Brevicoryne brassicae), rosy apple aphid(Dysaphis plantaginea), false cabbage aphid (Lipaphis erysimi), potatoaphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani),lettuce aphid (Nasonovia ribisnigri), grain aphid (Rhopalosiphum padi),corn aphid (Rhopalosiphum maidis), brown citrus aphid (Toxopteracitricida), mealy plum aphid (Hyalopterus pruni), cane aphid (Melanaphissacchari), black rice root aphid (Tetraneura nigriabdominalis),sugarcane cottony aphid (Ceratovacuna lanigera), and apple woolly aphid(Eriosoma lanigerum);

from the family Phylloxeridae, for example, grapevine phylloxera(Daktulosphaira vitifoliae), Pecan phylloxera (Phylloxera devastatrix),Pecan leaf phylloxera (Phylloxera notabilis), and Southern pecan leafphylloxera (Phylloxera russellae);

from the family Adelgidae, for example, hemlock woolly aphid (Adelgestsugae), Adelges piceae, and Aphrastasia pectinatae;

from the family Pentatomidae, for example, black rice bug (Scotinopharalurida), Malayan rice black bug (Scotinophara coarctata), common greenstink bug (Nezara antennata), white-spotted spined bug (Eysarcorisaeneus), lewis spined bug (Eysarcoris lewisi), white-spotted bug(Eysarcoris ventralis), Eysarcoris annamita, brown marmorated stink bug(Halyomorpha halys), green plant bug (Nezara viridula), Brown stink bug(Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebaluspugnax, and Dichelops melacanthus;

from the family Cydnidae, for example, Burrower brown bug (Scaptocoriscastanea);

from the family Alydidae, for example, bean bug (Riptortus pedestris),corbett rice bug (Leptocorisa chinensis), and rice bug (Leptocorisaacuta);

from the family Coreidae, for example, Cletus punctiger and Australianleaf-footed bug (Leptoglossus australis);

from the family Lygaeidae, for example, oriental chinch bug (Cavereliussaccharivorus), seed bug (Togo hemipterus), and chinch bug (Blissusleucopterus); from the family Miridae, for example, rice leaf bug(Trigonotylus caelestialium), sorghum plant bug (Stenotusrubrovittatus), wheat leaf bug (Stenodema calcarata), and Americantarnished plant bug (Lygus lineolaris);

from the family Aleyrodidae, for example, greenhouse whitefly(Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), citruswhitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthusspiniferus), tea spiny whitefly (Aleurocanthus camelliae), and Pealiuseuryae;

from the family Diaspididae, for example, Abgrallaspis cyanophylli, redscale (Aonidiella aurantii), San Jos6 scale (Diaspidiotus perniciosus),white peach scale (Pseudaulacaspis pentagona), arrowhead scale (Unaspisyanonensis), and citrus snow scale (Unaspis citri); from the familyCoccidae, for example, pink wax scale (Ceroplastes rubens);

from the family Margarodidae, for example, fluted scale (Iceryapurchasi) and seychelles fluted scale (Icerya seychellarum);

from the family Pseudococcidae, for example, solanum mealybug(Phenacoccus solani), cotton mealybug (Phenacoccus solenopsis), Japanesemealybug (Planococcus kraunhiae), white peach scale (Pseudococcuscomstocki), citrus mealybug (Planococcus citri), currant mealybug(Pseudococcus calceolariae), long-tailed mealybug (Pseudococcuslongispinus), and tuttle mealybug (Brevennia rehi); from the familyPsyllidae, for example, citrus psylla (Diaphorina citri), two-spottedcitrus psyllid (Trioza erytreae), pear sucker (Cacopsylla pyrisuga),Cacopsylla chinensis, potato psyllid (Bactericera cockerelli), and Pearpsylla (Cacopsylla pyricola);

from the family Tingidae, for example, sycamore lace bug (Corythuchaciliata), aster tingid (Corythucha marmorata), Japanese pear lace bug(Stephanitis nashi), and azalea lace bug (Stephanitis pyrioides);

from the family Cimicidae, for example, common bed bug (Cimexlectularius);

from the family Cicadidae, for example, Giant Cicada (Quesada gigas);Triatoma spp. (such as Triatoma infestans); and the others.

Lepidoptera:

from the family Crambidae, for example, rice stem borer (Chilosuppressalis), Dark-headed stem borer (Chilo polychrysus), white stemborer (Scirpophaga innotata), yellow paddy borer (Scirpophagaincertulas), Rupela albina, rice leaf roller (Cnaphalocrocis medinalis),Marasmia patnalis, rice leaf roller (Marasmia exigua), cotton leafroller (Notarcha derogata), corn borer (Ostrinia furnacalis), Europeancorn borer (Ostrinia nubilalis), cabbage webworm (Hellula undalis),grape leafroller (Herpetogramma luctuosale), bluegrass webworm (Pediasiateterrellus), rice case-worm (Nymphula depunctalis), and Sugarcane borer(Diatraea saccharalis);

from the family Pyralidae, for example, lesser cornstalk borer(Elasmopalpus lignosellus), mealworm moth (Plodia interpunctella), andpersimmon bark borer (Euzophera batangensis);

from the family Noctuidae, for example, cotton worm (Spodoptera litura),beet armyworm (Spodoptera exigua), rice armyworm (Mythimna separata),cabbage moth (Mamestra brassicae), pink borer (Sesamia inferens), grassarmyworm (Spodoptera mauritia), green rice caterpillar (Narangaaenescens), Spodoptera frugiperda, true armyworm (Spodoptera exempta),black cutworm (Agrotis ipsilon), beet worm (Autographa nigrisigna), ricelooper (Plusia festucae) soybean looper (Chrysodeixis includens),Trichoplusia spp., Heliothis spp. (such as tobacco budworm (Heliothisvirescens)), Helicoverpa spp. (such as tobacco budworm (Helicoverpaarmigera) and corn earworm (Helicoverpa zea)), Velvetbean caterpillar(Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), and Hopvine borer (Hydraecia immanis);

from the family Pieridae, for example, common cabbage worm (Pierisrapae);

from the family Tortricidae, for example, oriental fruit moth(Grapholita molesta), Grapholita dimorpha, soybean moth (Leguminivoraglycinivorella), Matsumuraeses azukivora, summer fruit tortrix(Adoxophyes orana fasciata) smaller tea tortrix (Adoxophyes honmai),Japanese tea tortrix (Homona magnanima), apple tortrix (Archipsfuscocupreanus), codling moth (Cydia pomonella), sugarcane shoot borer(Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema), andCitrus fruit borer (Ecdytolopha aurantiana);

from the family Gracillariidae, for example, tea leaf roller (Caloptiliatheivora) and Asiatic apple leaf miner (Phyllonorycter ringoniella);

from the family Carposinidae, for example, peach fruit moth (Carposinasasakii);

from the family Lyonetiidae, for example, Coffee Leaf miner (Leucopteracoffeella), peach leaf miner (Lyonetia clerkella), and Lyonetiaprunifoliella;

from the family Lymantriidae, for example, Lymantria spp. (such as gypsymoth (Lymantria dispar)) and Euproctis spp. (such as tea lymantriid(Euproctis pseudoconspersa)); from the family Plutellidae, for example,diamondback moth (Plutella xylostella);

from the family Gelechiidae, for example, peach worm (Anarsialineatella), sweetpotato leaf folder (Helcystogramma triannulella), pinkbollworm (Pectinophora gossypiella), potato moth (Phthorimaeaoperculella), and Tuta absoluta;

from the family Arctiidae, for example, American white moth (Hyphantriacunea);

from the family Castniidae, for example, Giant Sugarcane borer (Telchinlicus);

from the family Cossidae, for example, Cossus insularis;

from the family Geometridae, for example, Ascotis selenaria;

from the family Limacodidae, for example, blue-striped nettle grub(Parasa lepida);

from the family Stathmopodidae, for example, persimmon fruit moth(Stathmopoda masinissa);

from the family Sphingidae, for example, tobacco hornworm (Acherontialachesis);

from the family Sesiidae, for example, Nokona feralis, cherry borer(Synanthedon hector), and Synanthedon tenuis:

from the family Hesperiidae, for example, rice skipper (Parnaraguttata);

from the family Tineidae, for example, casemaking clothes moth (Tineatranslucens) and common clothes moth (Tineola bisselliella);

and the others.

Thysanoptera:

from the family Thripidae, for example, western flower thrips(Frankliniella occidentalis), oriental thrips (Thrips palmi), yellow teathrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), easternflower thrips (Frankliniella intonsa), rice thrips (Stenchaetothripsbiformis), and Echinothrips americanus;

from the family Phlaeothripidae, for example, aculeated rice thrips(Haplothrips aculeatus);

and the others.

Diptera:

from the family Anthomyiidae, for example, seedcorn maggot (Deliaplatura), onion maggot (Delia antiqua), and beet leaf miner (Pegomyacunicularia);

from the family Ulidiidae, for example, sugarbeet root maggot (Tetanopsmyopaeformis);

from the family Agromyzidae, for example, rice leaf miner (Agromyzaoryzae), tomato leaf miner (Liriomyza sativae), chrysanthemum leaf miner(Liriomyza trifolii), and pea leafminer (Chromatomyia horticola);

from the family Chloropidae, for example, rice stem maggot (Chloropsoryzae);

from the family Tephritidae, for example, melon fly (Bactroceracucurbitae), oriental fruit fly (Bactrocera dorsalis), Malaysian fruitfly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae),Queensland fruit fly (Bactrocera tryoni), Mediterranean fruit fly(Ceratitis capitata), apple maggot (Rhagoletis pomonella), and Japanesecherry fruit fly (Rhacochlaena japonica);

from the family Ephydridae, for example, smaller rice leaf miner(Hydrellia griseola), whorl maggot (Hydrellia philippina), and paddystem maggot (Hydrellia sasakii);

from the family Drosophilidae, for example, cherry drosophila(Drosophila suzukii);

from the family Phoridae, for example, Megaselia spiracularis;

from the family Psychodidae, for example, Clogmia albipunctata;

from the family Sciaridae, for example, Bradysia difformis;

from the family Cecidomyiidae, for example, hessian fly (Mayetioladestructor) and paddy gall fly (Orseolia oryzae);

from the family Diopsidae, for example, Diopsis macrophthalma;

from the family Tipulidae, for example, rice crane fly (Tipula aino),Common cranefly (Tipula oleracea), and European cranefly (Tipulapaludosa);

from the family Culicidae, for example, southern house mosquito (Culexpipiens pallens), dengue mosquito (Aedes aegypti), Asian tiger mosquito(Aedes albopictus), Chinese malaria mosquito (Anopheles hyracanussinensis), Culex quinquefasciatus, Culex pipiens molestus Forskal, andbrown house mosquito (Culex quinquefasciatus);

from the family Simulidae, for example, Prosimulium yezoensis andSimulium ornatum;

from the family Tabanidae, for example, Tabanus trigonus;

from the family Muscidae, for example, house fly (Musca domestica),false stable fly (Muscina stabulans), biting house fly (Stomoxyscalcitrans), and buffalo fly (Haematobia irritans);

from the family Calliphoridae;

from the family Sarcophagidae;

from the family Chironomidae, for example, Chironomus plumosus,Chironomus yoshimatsui, and Glyptotendipes tokunagai;

from the family Fannidae;

and the others.

Coleoptera:

from the family Chrysomelidae, for example, western corn rootworm(Diabrotica virgifera virgifera), southern corn rootworm (Diabroticaundecimpunctata howardi), northern corn rootworm (Diabrotica barberi),Mexican corn rootworm (Diabrotica virgifera zeae), banded cucumberbeetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa),bean leaf beetle (Cerotoma trifurcata), barley leaf beetle (Oulemamelanopus), cucurbit leaf beetle (Aulacophora femoralis), striped fleabeetle (Phyllotreta striolata), Cabbage flea beetle (Phyllotretacruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbagestem flea beetle (Psylliodes chrysocephala), Colorado potato beetle(Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), grapecolaspis (Colaspis brunnea), corn flea beetle (Chaetocnema pulicaria),sweet-potato flea beetle (Chaetocnema confinis), potato flea beetle(Epitrix cucumeris), rice leaf beetle (Dicladispa armigera), southerncorn leaf beetle (Myochrous denticollis), Laccoptera quadrimaculata, andtobacco flea beetle (Epitrix hirtipennis);

from the family Carabidae, for example, Seedcorn beetle (Stenolophuslecontei) and slender seed-corn ground beetle (Clivina impressifrons);

from the family Scarabaeidae, for example, cupreus chafer (Anomalacuprea), soybean beetle (Anomala rufocuprea), Anomala albopilosa,Japanese beetle (Popillia japonica), yellowish elongate chafer(Heptophylla picea), European Chafer (Rhizotrogus majalis), Tomarusgibbosus, Holotrichia spp., Phyllophaga spp. (such as June beetle(Phyllophaga crinita)), and Diloboderus spp. (such as Diloboderusabderus);

from the family Curculionidae, for example, coffee bean weevil(Araecerus coffeae), sweet-potato weevil (Cylas formicarius), WestIndian sweet-potato weevil (Euscepes postfasciatus), alfalfa weevil(Hypera postica), maize wevil (Sitophilus zeamais), rice plant weevil(Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus),Rhabdoscelus lineatocollis, boll weevil (Anthonomus grandis), nuntingbillbug (Sphenophorus venatus), Southern Corn Billbug (Sphenophoruscallosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcaneweevil (Sphenophorus levis), rusty gourd-shaped weevil (Scepticusgriseus), brown gourd-shaped weevil (Scepticus uniformis), Mexican beanweevil (Zabrotes subfasciatus), pine beetle (Tomicus piniperda), CoffeeBerry Borer (Hypothenemus hampei), Aracanthus spp. (such as Aracanthusmourei), and cotton root borer (Eutinobothrus brasiliensis);

from the family Tenebrionidae, for example, red meal beetle (Triboliumcastaneum) and mason beetle (Tribolium confusum);

from the family Coccinellidae, for example, twenty-eight-spottedladybird (Epilachna vigintioctopunctata); from the family Bostrychidae,for example, common powder-post beetle (Lyctus brunneus);

from the family Ptinidae;

from the family Cerambycidae, for example, citrus long-horned beetle(Anoplophora malasiaca) and Migdolus fryanus;

from the family Elateridae, for example, Melanotus okinawensis, barleywireworm (Agriotes fuscicollis), Melanotus legatus, Anchastus spp.,Conoderus spp., Ctenicera spp., Limonius spp., and Aeolus spp.; from thefamily Staphylinidae, for example, Paederus fuscipes;

from the family Dermestidae, for example, varied carpet beetle(Anthrenus verbasci) and hide beetle (Dermestes maculates);

from the family Anobiidae, for example, tobacco beetle (Lasiodermaserricorne) and biscuit beetle (Stegobium paniceum);

and the others.

Orthoptera:

from the family Acrididae, for example, oriental migratory locust(Locusta migratoria), Moroccan locust (Dociostaurus maroccanus),Australian plague locust (Chortoicetes terminifera), red locust(Nomadacris septemfasciata), Brown Locust (Locustana pardalina), TreeLocust (Anacridium melanorhodon), Italian Locust (Calliptamus italicus),Differential grasshopper (Melanoplus differentialis), Two stripedgrasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplussanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum),Clearwinged grasshopper (Camnula pellucida), desert locust (Schistocercagregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throatedlocust (Austracris guttulosa), Japanese grasshopper (Oxya yezoensis),rice grasshopper (Oxya japonica), and Bombay locust (Patanga succincta);

from the family Gryllotalpidae, for example, oriental mole cricket(Gryllotalpa orientalis);

from the family Gryllidae, for example, house cricket (Acheta domestica)and emma field cricket (Teleogryllus emma);

from the family Tettigoniidae, for example, Mormon cricket (Anabrussimplex);

and the others.

Hymenoptera:

from the family Tenthredinidae, for example, beet sawfly (Athalia rosae)and nippon cabbage sawfly (Athalia japonica);

from the family Formicidae, for example, Solenopsis spp. (such as redimported fire ant (Solenopsis invicta) and tropical fire ant (Solenopsisgeminata)), Atta spp. (such as Brown leaf-cutting ant (Atta capiguara)),Acromyrmex spp., Paraponera clavata, black house ant (Ochetellusglaber), little red ant (Monomorium pharaonis), Argentine ant(Linepithema humile), Formica fusca japonica, Pristomyrmex punctutus,Pheidole noda, big-headed ant (Pheidole megacephala), Camponotus spp.(such as Camponotus japonicus and Camponotus obscuripes), Pogonomyrmexspp. (such as western harvester ant (Pogonomyrmex occidentalis))Wasmania spp. (such as Wasmania auropunctata), and long-legged ant(Anoplolepis gracilipes);

from the family Vespidae, for example, Asian giant hornet (Vespamandarinia japonica), Vespa simillima, Vespa analis Fabriciusi, Asianhornet (Vespa velutina), and Polistes jokahamae;

from the family Siricidae, for example, pine wood wasp (Urocerus gigas);

from the family Bethylidae;

and the others.

Blattodea:

from the family Blattellidae, for example, German cockroach (Blattellagermanica);

from the family Blattidae, for example, smoky-brown cockroach(Periplaneta fuliginosa), American cockroach (Periplaneta americana),brown cockroach (Periplaneta brunnea), and black cockroach (Blattaorientalis);

from the family Termitidae, for example, Japanese termite(Reticulitermes speratus), Formosan termite (Coptotermes formosanus),western drywood termite (Incisitermes minor), Cryptotermes domesticus,Odontotermes formosanus, Neotermes koshunensis, Glyptotermessatsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsissjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus,Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermestakasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, andCornitermes cumulans; and the others.

Siphonaptera:

cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis),human flea (Pulex irritans), oriental rat flea (Xenopsylla cheopis),chigoe flea (Tunga penetrans), chicken flea (Echidnophaga gallinacea),and European rat flea (Nosopsyllus fasciatus);

and the others.

Anoplura:

pig louse (Haematopinus suis), short-nosed cattle louse (Haematopinuseurysternus), Dalmalinia ovis, Linognathus seypsus, Pediculus humanis,Pediculuc humanus corporis, Pediculus humanus humanus, and Phthiruspubis;

and the others.

Mallophagida:

Bovicola spp. (such as Dalmalinia bovis and Dalmalinia ovis),Trichodectes spp. (such as Trichodectes canis), Felicola spp. (such asFelicola subrostrata), and Lipeurus spp. (such as Lipeurus caponis);

from the family Menoponidae, for example, Trimenopon spp. and Menoponspp.;

and the others.

Acari:

from the family Tetranychidae, for example, common red spider mite(Tetranychus urticae), kanzawa spider mite (Tetranychus kanzawai), redspider mite (Tetranychus evansi), citrus red mite (Panonychus citri),fruit-tree red spider mite (Panonychus ulmi), and Oligonychus spp.;

from the family Eriophyidae, for example, Japanese citrus rust mite(Aculops pelekassi), Phyllocoptruta citri, tomato mite (Aculopslycopersici), purple mite (Calacarus carinatus), tea rust mite(Acaphylla theavagrans), Eriophyes chibaensis, apple bud mite (Aculusschlechtendali), Aceria diospyri, Aceria tosichella, and Shevtchenkellasp.;

from the family Tarsonemidae, for example, broad mite(Polyphagotarsonemus latus);

from the family Tenuipalpidae, for example, Brevipalpus phoenicis;

from the family Tuckerellidae;

from the family Ixodidae, for example, Haemaphysalis longicornis,Haemaphysalis flava, Dermacentor taiwanensis, American dog tick(Dermacentor variabilis), Dermacentor andersoni, Ixodes ovatus, Ixodespersulcatus, Ixodes ricinus, black-legged tick (Ixodes scapularis), lonestar tick (Amblyomma americanum), gulf coast tick (Amblyomma maculatum),Boophilus microplus, Boophilus annulatus, and brown dog tick(Rhipicephalus sanguineus);

from the family Acaridae, for example, cereal mite (Tyrophagusputrescentiae) and grassland mite (Tyrophagus similis);

from the family Pyroglyphidae, for example, American house dust mite(Dermatophagoides farinae) and European house dust mite(Dermatophagoides pteronyssinus); from the family Cheyletidae, forexample, Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei,and Cheyletiella yasguri;

from the family Sarcoptidae, for example, mange mite (Otodectes cynotis)and itch mite (Sarcoptes scabiei); from the family Demodicidae, forexample, dog follicle mite (Demodex canis);

from the family Listrophoridae;

from the family Haplochthoniidae;

from the family Macronyssidae, for example, tropical rat mite(Ornithonyssus bacoti) and feather mite (Ornithonyssus sylviarum);

from the family Dermanyssidae, for example, bird mite (Dermanyssusgallinae);

from the family Trombiculidae, for example, Leptotrombidium akamushi;

and the others.

Araneae:

from the family Eutichuridae, for example, Cheiracanthium japonicum;

from the family Theridiidae, for example, red-back spider (Latrodectushasseltii);

and the others.

Polydesmida:

from the family Paradoxosomatidae, for example, flat-backed millipede(Oxidus gracilis) and Nedyopus tambanus;

and the others.

Isopoda:

from the family Armadillidiidae, for example, common pill bug(Armadillidium vulgare);

and the others.

Chilopoda:

from the family Scutigeridae, for example, Thereuonema hilgendorfi;

from the family Scolopendridae, for example, giant tropical centipede(Scolopendra subspinipes);

from the family Ethopolyidae, for example, Bothropolys rugosus;

and the others.

Gastropoda:

from the family Limacidae, for example, tree slug (Limax marginatus) andgarden tawny slug (Limax flavus); from the family Philomycidae, forexample, Meghimatium bilineatum;

from the family Ampullariidae, for example, golden apple snail (Pomaceacanaliculata);

from the family Lymnaeidae, for example, Austropeplea ollula;

and the others.

Nematoda:

from the family Aphelenchoididae, for example, rice white-tip nematode(Aphelenchoides besseyi);

from the family Pratylenchidae, for example, root lesion nematode(Pratylenchus coffeae), Pratylenchus brachyurus, California meadownematode (Pratylenchus neglectus), and Radopholus similis;

from the family Heteroderidae, for example, javanese root-knot nematode(Meloidogyne javanica), southern root-knot nematode (Meloidogyneincognita), northern root-knot nematode (Meloidogyne hapla), soybeancyst nematode (Heterodera glycines), potato cyst nematode (Globoderarostochiensis), and white potato cyst nematode (Globodera pallida);

from the family Hoplolaimidae, for example, Rotylenchulus reniformis;

from the family Anguinidae, for example, strawberry bud nematode(Nothotylenchus acris) and stem nematode (Ditylenchus dipsaci);

from the family Tylenchulidae, for example, citrus nematode (Tylenchulussemipenetrans);

from the family Longidoridae, for example, dagger nematode (Xiphinemaindex);

from the family Trichodoridae;

from the family Parasitaphelenchidae, for example, pine wilt disease(Bursaphelenchus xylophilus);

and the others.

The target harmful arthropods such as harmful insects and harmful mites,harmful mollusks, and harmful nematodes may have a reducedagent-sensitivity to or a developed agent-resistance to an insecticide,a miticide, a molluscicide or a nematicide. However, when theagent-sensitivity is greatly reduced or the agent-resistance is greatlydeveloped, a composition comprising an insecticide, a miticide, amolluscicide, and a nematicide other than the intended insecticide,miticide, molluscicide, and nematicide is preferably used.

The Present compounds X may be also used to protect plants from plantdiseases caused by insect-borne viruses or insect-borne bacteria.

Examples of the insect-borne viruses are recited as follows.

Rice tungro spherical virus, Rice tungro bacilliform virus, Rice grassystunt virus, Rice ragged stunt virus, Rice stripe virus, Rice blackstreaked dwarf virus, Southern rice black-streaked dwarf virus, Ricegall dwarf virus, Rice hoja blanca virus, Rice yellow stunt virus, Riceyellow mottle virus, Rice dwarf virus, Northern cereal mosaic virus,Barley yellow dwarf virus, Barley mild mosaic virus, Barley yellow dwarfvirus-PAV, Cereal yellow dwarf virus-RPS, Wheat yellow leaf virus, Oatsterile dwarf virus, Wheat streak mosaic virus, Maize dwarf mosaicvirus, Maize stripe virus, Maize chlorotic mottle virus, Maize chloroticdwarf virus, Maize rayado fino virus, Sugarcane mosaic virus, Fijidisease virus, Sugarcane yellow leaf virus, Soybean mild mosaic virus,Cycas necrotic stunt virus, Soybean dwarf virus, Milk vetch dwarf virus,Soybean mosaic virus, Alfalfa mosaic virus, Bean yellow mosaic virus,Bean common mosaic virus, Southern bean mosaic virus, Peanut stuntvirus, Broad bean wilt virus 1, Broad bean wilt virus 2, Broad beannecrosis virus, Broad bean yellow vein virus, Clover yellow vein virus,Peanut mottle virus, Tobacco streak virus, Bean pod mottle virus, Cowpeachlorotic mottle virus, Mung bean yellow mosaic virus, Soybean crinkleleaf virus, Tomato chlorosis virus, Tomato spotted wilt virus, Tomatoyellow leaf curl virus, Tomato aspermy virus, Tomato infectiouschlorosis virus, Potato leafroll virus, Potato virus Y, Melon yellowspot virus, Melon necrotic spot virus, Watermelon mosaic virus, Cucumbermosaic virus, Zucchini yellow mosaic virus, Turnip mosaic virus, Turnipyellow mosaic virus, Cauliflower mosaic virus, Lettuce mosaic virus,Celery mosaic virus, Beet mosaic virus, Cucurbit chlorotic yellowsvirus, Capsicum chlorosis virus, Beet pseudo yellows virus, Leak yellowstripe virus, Onion yellow dwarf virus, Sweet potato feathery mottlevirus, Sweet potato shukuyo mosaic virus, Strawberry mottle virus,Strawberry mild yellow edge virus, Strawberry pseudo mild yellow edgevirus, Strawberry crinkle virus, Strawberry vein banding virus, Plum poxvirus, Chrysanthemum stem necrosis virus, Impatiens necrotic spot virus,Iris yellow spot virus, Lily mottle virus, Lilly symptomless virus,Tulip mosaic virus, and the others.

Examples of the insect-borne bacteria are recited as follows.

Candidatus Phytoplasma oryzae, Candidatus Phytoplasma asteris, Maizebushy stunt phytoplasma, Candidatus Liberbacter asiaticus, CandidatusLiberbacter africanus, Candidatus Liberbacter americanus, and theothers.

The composition for controlling harmful arthropods of the presentinvention comprises the Present compound, the Present compound X, or theComposition A and inert carrier(s) (hereinafter referred to as “Presentcomposition”). The Present composition is usually prepared by mixing thePresent compound, the Present compound X, or the Composition A withinert carrier(s) such as solid carrier(s), liquid carrier(s), andgaseous carrier(s), and as needed, adding surfactant(s) and otherauxiliary agent(s) for formulation, to formulate into an emulsifiableconcentrate, an oil solution, a dust formulation, a granule, a wettablepowder, a granular wettable powder, a flowable, a dry flowable, amicrocapsule, an aerosol, a poison bait, a resin formulation, a shampooformulation, a paste-like formulation, a foam, a carbon dioxideformulation, a tablet, or the like. Such formulation may be processedinto and used as a mosquito repellent coil, an electric mosquitorepellent mat, a liquid mosquito repellent formulation, a smoking agent,a fumigant, a sheet formulation, a spot-on formulation, or a formulationfor oral treatment. The Present composition usually comprises 0.0001 to95% by weight of the Present compound, the Present compound X, or theComposition A.

Examples of the solid carrier(s) to be used in the formulation includefine powders and granules of clays (for example, kaolin clay,diatomaceous earth, bentonite, Fubasami clay, and acid white clay), drysilica, wet silica, talc, ceramic, other inorganic minerals (forexample, sericite, quartz, sulfur, active carbon, and calciumcarbonate), chemical fertilizers (for example, ammonium sulfate,ammonium phosphate, ammonium nitrate, urea, and ammonium chloride), andthe others; as well as synthetic resins (for example, polyester resinssuch as polypropylene, polyacrylonitrile, polymethylmethacrylate, andpolyethylene terephthalate; nylon resins such as nylon-6, nylon-11, andnylon-66; polyamide resins; polyvinyl chloride, polyvinylidene chloride,vinyl chloride-propylene copolymers, and the others).

Examples of the liquid carrier(s) include water; alcohols (for example,methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol,ethylene glycol, propylene glycol, and phenoxy ethanol); ketones (forexample, acetone, methyl ethyl ketone, and cyclohexanone); aromatichydrocarbons (for example, toluene, xylene, ethyl benzene, dodecylbenzene, phenyl xylyl ethane, and methylnaphthalene); aliphatichydrocarbons (for example, hexane, cyclohexane, kerosene, and lightoil); esters (for example, ethyl acetate, butyl acetate, isopropylmyristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, andpropylene glycol monomethyl ether acetate); nitriles (for example,acetonitrile and isobutyronitrile); ethers (for example, diisopropylether, 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethylether, diethylene glycol monomethyl ether, propylene glycol monomethylether, dipropylene glycol monomethyl ether, and3-methoxy-3-methyl-1-butanol); amides (for example, DMF andN,N-dimethylacetamide); sulfoxides (for example, DMSO); propylenecarbonate; and vegetable oils (for example, soybean oil and cottonseedoil).

Examples of the gaseous carrier(s) include fluorocarbon, butane gas, LPG(liquefied petroleum gas), dimethyl ether, and carbon dioxide.

Examples of the surfactant(s) include nonionic surfactants such aspolyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, andpolyethylene glycol fatty acid esters; and anionic surfactants such asalkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

Examples of the other auxiliary agent(s) for formulation includebinders, dispersants, colorants, and stabilizers. Specific examplesthereof include casein, gelatin, saccharides (for example, starch, gumarabic, cellulose derivatives, and alginic acid), lignin derivatives,bentonite, water-soluble synthetic polymers (for example, polyvinylalcohol, polyvinyl pyrrolidone, and polyacrylic acids), acidic isopropylphosphate, 2,6-di-tert-butyl-4-methylphenol, and BHA (a mixture of2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of the base material of the resin formulation include vinylchloride polymers, polyurethane, and the others, and plasticizer(s) suchas phthalic acid esters (for example, dimethyl phthalate and dioctylphthalate), adipic acid esters, and stearic acid may also be added tothese base materials, as needed. The resin formulation may be preparedby mixing a compound with the above-mentioned base material, kneadingthe mixture in a conventional kneading apparatus, followed by molding itby injection molding, extrusion molding, pressure molding, or the like.The resultant resin formulation may be subjected to further molding,cutting procedure, or the like, as needed, to be processed into a shapesuch as plate, film, tape, net, and string shapes. These resinformulations may be processed into an animal collar, an animal ear tag,a sheet formulation, a trap string, a gardening support, or otherproducts.

Examples of the base material for the poison bait include grain powders,vegetable oils, saccharides, crystalline celluloses, and the others, andfurther, antioxidant(s) such as dibutylhydroxytoluene andnordihydroguaiaretic acid, preservative(s) such as dehydroacetic acid,accidental ingestion inhibitor(s) for children and pets such as chilipowder, insect attraction fragrance(s) such as cheese flavor, onionflavor, and peanut oil, or the other ingredient(s) may be added theretoas needed.

The method for controlling harmful arthropods of the present inventionis carried out by applying an effective amount of the Present compound,the Present compound X, or the Composition A to harmful arthropodsdirectly and/or habitats where harmful arthropods live (for example,plant bodies, soil, interiors of houses, and animal bodies). Also, thePresent compound may be applied to seeds. Examples of the method forcontrolling harmful arthropods of the present invention include foliagetreatment, soil treatment, root treatment, shower treatment, smokingtreatment, water surface treatment, and seed treatment.

In the present invention, examples of the plants include whole plants,foliages, flowers, ears, fruits, tree stems, branches, tree crowns,seeds, vegetative reproduction organs, and seedlings.

A vegetative reproduction organ means a part of plant such as root,stem, and leaf which has a growth capability even when said part isseparated from the plant body and placed into soil. Examples of thevegetative reproduction organ include tuberous root, creeping root,bulb, corm or solid bulb, tuber, rhizome, stolon, rhizophore, canecuttings, propagule, and vine cutting. Stolon is also referred to as“runner”, and propagule is also referred to as “propagulum” andcategorized into broad bud and bulbil. Vine cutting means a shoot(collective term of leaf and stem) of sweet potato, glutinous yam, orthe like. Bulb, corm or solid bulb, tuber, rhizome, cane cuttings,rhizophore, and tuberous root are also collectively referred to as“bulb”. For example, cultivation of potato starts with planting a tuberinto soil, and the tuber to be used is generally referred to as “seedpotato”.

Examples of the method for controlling harmful arthropods by applying aneffective amount of the Present compound, the Present compound X, or theComposition A to soil include a method for applying an effective amountof the composition of the present invention to soil before or afterplanting plants, a method for applying an effective amount of thecomposition of the present invention to rhizosphere of crops to beprotected from harm such as eating by harmful arthropods, and, a methodfor controlling plant-eating harmful arthropods by impregnating aneffective amount of the composition of the present invention from rootsor the like and migrating it to inside plant bodies. More specificexamples thereof include planting hole treatments (for example, plantinghole application and planting hole soil incorporation), plant foottreatments (for example, plant foot application, plant foot soilincorporation, plant foot irrigation, and plant foot treatment at latterhalf of raising of seedling period), planting trench treatments (forexample, planting trench application and planting trench soilincorporation), row treatments (for example, row application, row soilincorporation, and row application at growing season), row treatments atseeding (for example, row application at seeding and row soilincorporation at seeding), overall treatments (for example, overall soilapplication and overall soil incorporation), side row treatments, watersurface treatments (for example, water surface application and watersurface application after flooding), other soil application treatments(for example, foliar application of granule at growing season,application under tree crown or around trunk, soil surface application,soil surface incorporation, seeding hole application, ridge area surfaceapplication, and intrarow spacing application), other irrigationtreatments (for example, soil irrigation, irrigation at raising ofseedling period, chemical injection treatment, ground area irrigation,chemical drip irrigation, and chemigation), raising seedling boxtreatments (for example, raising seedling box application, raisingseedling box irrigation, raising seedling box chemical flooding),raising seedling tray treatments (for example, raising seedling trayapplication, raising seedling tray irrigation, and raising seedling traychemical flooding), nursery treatments (for example, nurseryapplication, nursery irrigation, flooded nursery application, andseedling soaking), bed soil incorporation treatments (for example, bedsoil incorporation, bed soil incorporation before seeding, applicationat seeding before soil covering, application at seeding after soilcovering, and soil covering incorporation), and other treatments (forexample, culture soil incorporation, plowing, surface soilincorporation, rain dropping point soil incorporation, planting positiontreatment, flower cluster application of granule, and paste fertilizerincorporation).

When the Present composition is used for controlling harmful arthropodsin the agricultural field, the application dose as an amount of thePresent compound or the Present compound X is usually within the rangefrom 1 to 10,000 g per 10,000 m². When the Present composition isapplied to seeds or vegetative reproduction organs, the application doseas an amount of the Present compound or the Present compound X isusually within the range from 0.001 to 100 g per 1 Kg of the seeds orvegetative reproduction organs. An emulsifiable concentrate, a wettablepowder, a flowable, or the like of the Present composition is usuallyapplied by diluting it with water in such a way that a concentration ofthe active ingredient is within the range from 0.01 to 10,000 ppm. Agranule, a dust formulation, or the like is usually applied as itselfwithout diluting it.

These formulations and diluents of the formulations with water may bedirectly sprayed to harmful arthropods or plants such as crops to beprotected from harmful arthropods, or applied to soil in cultivatedareas to control harmful arthropods that inhabit the soil.

Also, a resin formulation processed into a sheet shape or a string shapemay be wrapped around crops, stretched near crops, spread on plant footsoil, or the like.

When the Present composition is used to control harmful arthropods thatlive inside a house, the application dose as an amount of the Presentcompound or the Present compound X is usually within the range from 0.01to 1,000 mg per 1 m² of an area to be treated in the case of using it ona planar area. In the case of using it spatially, the application doseas an amount of the Present compound or the Present compound X isusually within the range from 0.01 to 500 mg per 1 m³ of the space to betreated. When the Present composition is formulated into an emulsifiableconcentrate, a wettable powder, a flowable, or the like, suchformulation is usually applied after diluting it with water in such away that a concentration of the active ingredient is within the rangefrom 0.1 to 10,000 ppm, and then sparging it. In the case of beingformulated into an oil solution, an aerosol, a smoking agent, a poisonbait, or the like, such formulation is used as itself without dilutingit.

When the Present composition is used for controlling external parasitesof livestock such as cows, horses, pigs, sheep, goats, and chickens, andsmall animals such as dogs, cats, rats, and mice, the Presentcomposition may be applied to the animals by a known method in theveterinary field. Examples of the specific method for using the Presentcomposition include administration by a tablet, a mixture with feed, asuppository, or an injection (for example, intramuscular, subcutaneous,intravenous, or intraperitoneal injection) when systemic control isintended, and include spraying of an oil solution or an aqueous liquid,pour-on treatment or spot-on treatment, washing of animals with ashampoo formulation, or application of a resin formulation in the formof a collar, an ear tag, or the like to animals when non-systemiccontrol is intended. In case of administered to animals, the dose of thePresent compound or the Present compound X is usually within the rangefrom 0.1 to 1,000 mg per 1 kg of animal body weight.

Also, the Present compound, the Present compound X, or the Composition Amay be used as an agent for controlling harmful arthropods in croplandssuch as fields, paddy fields, grasses, and orchards. Examples of theplants include the followings.

Crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean,peanut, buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco, andthe others; Vegetables: solanaceous vegetables (for example, eggplant,tomato, pimento, pepper, and potato), cucurbitaceous vegetables (forexample, cucumber, pumpkin, zucchini, water melon, and melon),cruciferous vegetables (for example, Japanese radish, white turnip,horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli,and cauliflower), asteraceous vegetables (for example, burdock, crowndaisy, artichoke, and lettuce), liliaceous vegetables (for example,welsh onion, onion, garlic, and asparagus), ammiaceous vegetables (forexample, carrot, parsley, celery, and parsnip), chenopodiaceousvegetables (for example, spinach and Swiss chard), lamiaceous vegetables(for example, perilla, mint, and basil), strawberry, sweet potato,glutinous yam, eddoe, and the others;

Flowers;

Foliage plants;

Fruits: pomaceous fruits (for example, apple, pear, Japanese pear,Chinese quince, and quince), stone fleshy fruits (for example, peach,plum, nectarine, Japanese apricot (Prunus mume), cherry fruit, apricot,and prune), citrus fruits (for example, Citrus unshiu, orange, lemon,lime, and grapefruit), nuts (for example, chestnuts, walnuts, hazelnuts,almond, pistachio, cashew nuts, and macadamia nuts), berry fruits (forexample, blueberry, cranberry, blackberry, and raspberry), grapes,Japanese persimmon, olive, Japanese plum, banana, coffee, date palm,coconuts, and the others; and

Trees other than fruit trees: tea, mulberry, flowering plants, roadsidetrees (for example, ash, birch, dogwood, eucalyptus, ginkgo (Ginkgobiloba), lilac, maple, oak (quercus), poplar, Judas tree, Formosan gum(Liquidambar formosana), plane tree, zelkova, Japanese arborvitae (Thujastandishii), fir wood, hemlock, juniper, pinus, picea, and yew (Taxuscuspidate)), and the others.

The above plants also include plants which may be produced by naturalbreeding, plants which may be generated by mutation, F1 hybrid plants,and genetically modified crops. Examples of the genetically modifiedcrops include plants which have resistance to HPPD(4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such asisoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyrand thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphatesynthase) inhibitors, glutamine synthetase inhibitors, PPO(protoporphyrinogen oxidase) inhibitors, or herbicide such as bromoxyniland dicamba; plants which can synthesize a selective toxin known inBacillus such as Bacillus thuringiensis or the like; and plants whichcan synthesize a gene fragment or the like which is partially identicalto an endogenous gene derived from a harmful insect, and induce a genesilencing (RNAi; RNA interference) in the target harmful insect toachieve a specific insecticidal activity.

The above plants are not specifically limited as long as they aregenerally cultivated cultivars.

EXAMPLES

The following Examples including Preparation Examples, FormulationExamples, and Test Examples serve to illustrate the present inventionmore in detail, but the present invention is not limited to theseExamples only.

First, Preparation Examples of the Present compounds X are shown below.

In the present description, Me represents a methyl group, Et representsan ethyl group, Pr represents a propyl group, i-Pr represents anisopropyl group, c-Pr represents a cyclopropyl group, Ph represents aphenyl group, Py2 represents a 2-pyridyl group, Py3 represents a3-pyridyl group, Py4 represents a 4-pyridyl group, and Bn represents abenzyl group. When c-Pr, Ph, Py2, Py3, and Py4 have substituent(s), thesubstituent(s) is/are indicated before the symbols with the substitutionposition(s). For example, 1-CN-c-Pr represents a 1-cyanocyclopropylgroup, 3,4-F₂-Ph represents a 3,4-difluorophenyl group, 4-CF₃—Py2represents a 4-(trifluoromethyl)-2-pyridyl group, and 5-OCH₂CF₂CF₃—Py2represents a 5-(2,2,3,3,3-pentafluoropropoxy)-2-pyridyl group.

Reference Preparation Example 1

A mixture of 4-amino-2-oxo-1,2-dihydropyrimidine (2.0 g),1-bromo-3,3,3-trifluoro-2-propanone (1.9 mL), and methanol (20 mL) wasadded to a vial, the vial was covered, and the mixture was stirred inmicrowave at 120° C. for 3 hours. The resulting mixture was cooled toroom temperature, water was added thereto, and the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was dried overanhydrous sodium sulfate, and concentrated under reduced pressure. Theresulting residue was subjected to silica gel chromatography to give theIntermediate compound A-1 represented by the following formula (0.5 g).

Intermediate compound A-1: ¹H-NMR (DMSO-d₆) δ: 11.89 (1H, s), 8.38 (1H,s), 7.41 (1H, d), 6.64 (1H, d).

Reference Preparation Example 1A

The following Intermediate compound A-13 was prepared according to theReference Preparation Example 1 by using1-bromo-3,3,4,4,4-pentafluoro-2-butanone instead of1-bromo-3,3,3-trifluoro-2-propanone.

Intermediate compound A-13: ¹H-NMR (CDCl₃) δ: 9.19 (1H, s), 8.11 (1H,s), 7.16 (1H, dd), 6.76 (1H, d).

Reference Preparation Example 2-1

A mixture of 3-chloro-2-aminopyrazine (1.0 g) and1-bromo-3,3,3-trifluoro-2-propanone (4.0 mL) in a closed container wasstirred at 100° C. for 10.5 hours. The resulting mixture was cooled toroom temperature, and filtered. The resulting solids were washed withhexane to give the Intermediate compound A-2 represented by thefollowing formula (2.45 g).

Intermediate compound A-2: ¹H-NMR (DMSO-d₆) δ: 8.36 (1H, s), 7.99 (1H,s), 5.05 (1H, d), 4.89 (1H, d).

Reference Preparation Example 2-2

A mixture of the Intermediate compound A-2 (2.16 g) and propionitrile(10 mL) was stirred under stirring for 2 hours. The resulting mixturewas cooled to room temperature, 2N hydrochloric acid was added theretountil the mixture became weakly acidic, and the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was dried overanhydrous sodium sulfate, and concentrated under reduced pressure togive the Intermediate compound A-3 represented by the following formula(1.32 g).

Intermediate compound A-3: ¹H-NMR (CDCl₃) δ: 8.10-8.09 (2H, m), 7.82(1H, t).

Reference Preparation Example 2-3

A mixture of the Intermediate compound A-3 (1.32 g), concentratedhydrochloric acid (3 mL), and water (1 mL) was stirred at 100° C. for 4hours. The resulting mixture was cooled to room temperature, theprecipitated solids were collected by filtration, and washedsequentially with water and chloroform to give the Intermediate compoundA-4 represented by the following formula (0.92 g).

Intermediate compound A-4: ¹H-NMR (DMSO-d₆) δ: 11.45 (1H, s), 8.42 (1H,d), 7.50 (1H, d), 6.99 (1H, d).

Reference Preparation Example 13

Under nitrogen atmosphere, to a mixture of2-(trifluoromethyl)pyrazolo[1,5-a]pyrazin-4(5H)-one (prepared accordingto the method described in WO 2006/023750 pamphlet) (0.20 g) and DMF (5mL) was added N-chlorosuccinimide (0.15 g) at room temperature, and theresulting mixture was stirred at room temperature for 2.5 hours and thenstirred at 80° C. for 1.5 hours. The resulting mixture was allowed tocool to room temperature, a saturated aqueous solution of sodiumhydrogen carbonate was added thereto, and the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was dried overanhydrous magnesium sulfate, and then concentrated under reducedpressure. The resulting residue was subjected to silica gel columnchromatography (hexane ethyl acetate=2:1) to give the Intermediatecompound A-5 represented by the following formula (0.18 g).

Intermediate compound A-5: ¹H-NMR (CDCl₃) δ: 9.81 (1H, br s), 7.46 (1H,s), 6.94 (1H, s).

Reference Preparation Example 13A

The following Intermediate compound A-6 was prepared according to theReference Preparation Example 13.

Intermediate compound A-6: ¹H-NMR (CDCl₃) δ: 10.15 (1H, br s), 7.49 (1H,s), 7.03 (1H, s).

Reference Preparation Example 14

Under nitrogen atmosphere, to a mixture of3-trifluoromethyl-1H-pyrazole-5-carboxylic acid methyl ester (0.58 g)and DMF (10 mL) was added N-bromosuccinimide (0.59 g), and the resultingmixture was stirred at 60° C. for 1 day. To the resulting mixture wereadded a 1 M aqueous solution of sodium thiosulfate and a saturatedaqueous solution of sodium hydrogen carbonate, and the resulting mixturewas extracted with tert-butyl methyl ether. The resulting organic layerwas dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The resulting residue was subjected to silica gelcolumn chromatography (hexane:ethyl acetate=2:1) to give theIntermediate compound A-7 represented by the following formula (0.53 g)

Intermediate compound A-7: ¹H-NMR (CDCl₃) δ: 11.35 (1H, br s), 4.02 (3H,s).

Reference Preparation Example 14A

The following Intermediate compound A-8 was prepared according to theReference Preparation Example 14.

Intermediate compound A-8: ¹H-NMR (CDCl₃) δ: 11.46 (1H, br s), 4.02 (3H,s).

Reference Preparation Example 15

Under nitrogen atmosphere, to a mixture of4-bromo-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid methyl ester(0.53 g), THE (2 mL), water (2 mL), and methanol (2 mL) was addedlithium hydroxide monohydrate (0.21 g) at room temperature, and theresulting mixture was stirred at room temperature for 1 hour. To theresulting mixture was added sodium hydroxide (0.21 g), and the resultingmixture was stirred at room temperature for 1 day. To the resultingmixture was added a saturated aqueous solution of sodium hydrogencarbonate, and the resulting mixture was extracted with ethyl acetate.To the resulting aqueous layer was added 1N hydrochloric acid, and theresulting mixture was extracted with ethyl acetate. The resultingorganic layer was dried over anhydrous magnesium sulfate, and thenconcentrated under reduced pressure to give the Intermediate compoundA-9 represented by the following formula (0.37 g).

Intermediate compound A-9: ¹H-NMR (DMSO-D₆) δ: 8.28 (1H, s)

Reference Preparation Example 15A

The following Intermediate compound A-10 was prepared according to theReference Preparation Example 15.

Intermediate compound A-10: ¹H-NMR (DMSO-D₆) δ: 7.21 (1H, s).

Reference Preparation Example 16

The following compound was synthesized according to the method describedin WO 2006/023750 pamphlet.

Intermediate compound A-11: ¹H-NMR (DMSO-D₆) δ: 10.98 (1H, s), 7.77 (1H,d), 7.10 (1H, d).

Intermediate compound A-12: ¹H-NMR (DMSO-D₆) δ: 7.79 (1H, d), 7.10 (1H,d).

Reference Preparation Example 3

To a mixture of 2,2,6,6-tetramethylpiperidine (17.5 mL) and THF (150 mL)was added dropwise a 1.6 M solution of butyllithium in hexane (64.4 mL)at −78° C. To the resulting mixture was added dropwise 2-fluoropyridine(10 g) at −78° C., and then the resulting mixture was stirred for 30minutes. Further, diethyl disulfide (12.7 mL) was added dropwise theretoat −78° C., and then the resulting mixture was stirred for 1 hour. Tothe resulting mixture was added a saturated aqueous solution of ammoniumchloride under ice-cooling, the resulting mixture was warmed to roomtemperature, and then extracted with ethyl acetate. The resultingorganic layer was washed with saturated brine, dried over anhydroussodium sulfate, and concentrated under reduced pressure. The resultingresidue was subjected to silica gel chromatography to give theIntermediate compound B-1 represented by the following formula (14.23g).

Intermediate compound B-1: ¹H-NMR (CDCl₃) δ: 8.03 (1H, td), 7.74-7.69(1H, m), 7.14 (1H, ddd), 2.97 (2H, q), 1.33 (3H, t).

Reference Preparation Example 4

To a mixture of sodium hydride (oily, 60%) (0.3 g),2,3-dichloro-5-(trifluoromethyl)pyridine (0.5 mL), and DMF (5 mL) wasadded dropwise ethanethiol (0.54 mL) under ice-cooling, and then theresulting mixture was stirred at 40° C. for 12 hours. To the resultingmixture was added a saturated aqueous solution of ammonium chloride, andthe resulting mixture was extracted with ethyl acetate. The resultingorganic layer was dried over anhydrous sodium sulfate, and concentratedunder reduced pressure. The resulting residue was subjected to silicagel chromatography to give the Intermediate compound B-3 represented bythe following formula (0.61 g).

Intermediate compound B-3: ¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 7.59 (1H,d), 3.24 (2H, q), 2.99 (2H, q), 1.39 (3H, t), 1.36 (3H, t).

Reference Preparation Example 5

THE following Intermediate compound B-5 was prepared according to theReference Preparation Example 4 by using5-bromo-2-chloro-3-fluoropyridine.

Intermediate compound B-5: ¹H-NMR (CDCl₃) δ: 8.19 (1H, d), 7.57 (1H, d),2.97 (2H, q), 1.42 (3H, t).

Reference Preparation Example 6

A mixture of the Intermediate compound B-5 (5.0 g),(trimethylsilyl)acetonitrile (5.4 mL), zinc fluoride (1.2 g),4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (1.14 g),tris(dibenzylideneacetone)dipalladium(0) (0.9 g), and DMF (10 mL) wasstirred at 100° C. for 5 hours. The resulting mixture was cooled to roomtemperature, water was added thereto, and the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was washedwith saturated brine, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography to give the Intermediate compound B-9represented by the following formula (2.63 g).

Intermediate compound B-9: ¹H-NMR (CDCl₃) δ: 8.08 (1H, d), 7.49 (1H, d),3.76 (2H, s), 3.00 (2H, q), 1.42 (3H, t).

Reference Preparation Example 7

A mixture of the Intermediate compound B-9 (3.27 g), 1,2-dibromoethane(1.6 mL), sodium hydride (oily, 60%) (1.29 g), and THF (30 mL) wasstirred at room temperature for 3 hours. To the resulting mixture wasadded water, and the resulting mixture was extracted with ethyl acetate.The resulting organic layer was dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography to give the Intermediate compound B-10represented by the following formula (2.17 g).

Intermediate compound B-10: ¹H-NMR (CDCl₃) δ: 7.97 (1H, d), 7.51 (1H,d), 3.01 (2H, q), 1.83 (2H, m), 1.46 (2H, m), 1.42 (3H, t).

Reference Preparation Example 8

To a mixture of the Intermediate compound B-1 (8.9 g) and chloroform(100 mL) was added 70% mCPBA (28.0 g) under ice-cooling, and theresulting mixture was stirred at room temperature for 12 hours. To theresulting mixture were added a saturated aqueous solution of sodiumhydrogen carbonate and a 1 M aqueous solution of sodium thiosulfate, andthe resulting mixture was extracted with chloroform. The resultingorganic layer was dried over anhydrous sodium sulfate, and concentratedunder reduced pressure. The resulting residue was subjected to silicagel chromatography to give the Intermediate compound B-2 represented bythe following formula (11.99 g).

Intermediate compound B-2: ¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.43-8.38(1H, m), 7.47-7.43 (1H, m), 3.38 (2H, q), 1.34 (3H, t).

Reference Preparation Example 9

The compounds prepared according to the Reference Preparation Example 8and the physical properties thereof are shown below.

A compound represented by formula (B-1)

wherein the combination of R³ and X^(b) represents any one combinationindicated in [Table B¹].

TABLE B1 Intermediate compound R³ X^(b) B-4 CF₃ S(O)₂Et B-6 Br Cl B-111-CN-c-Pr Cl

Intermediate compound B-4: ¹H-NMR (CDCl₃) δ: 9.17 (1H, s), 8.84 (1H, s),3.81-3.79 (2H, m), 3.71-3.67 (2H, m), 1.46-1.43 (3H, m), 1.41-1.36 (3H,m).

Intermediate compound B-6: ¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.56 (1H, d),3.51 (2H, q), 1.33 (3H, t).

Intermediate compound B-11: ¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.18 (1H,d), 3.51 (2H, q), 1.94-1.93 (2H, m), 1.55-1.53 (2H, m), 1.33 (3H, t).

Reference Preparation Example 10

A mixture of the Intermediate compound B-11 (1.09 g), cesium fluoride(1.2 g), and DMSO (10 mL) was stirred at 70° C. for 11 hours. To theresulting mixture was added water, and the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was dried overanhydrous sodium sulfate, and concentrated under reduced pressure. Theresulting residue was subjected to silica gel chromatography to give theIntermediate compound B-12 represented by the following formula (0.85g).

Intermediate compound B-12: ¹H-NMR (CDCl₃) δ: 8.54 (1H, dd), 8.17 (1H,dd), 3.38 (2H, q), 1.92-1.90 (2H, m), 1.55-1.53 (2H, m), 1.35 (3H, t).

Reference Preparation Example 11

The Intermediate compound B-7 represented by the following formula wasprepared according to the Reference Preparation Example 10.

Intermediate compound B-7: ¹H-NMR (CDCl₃) δ: 8.53 (1H, dd), 8.48 (1H,dd), 3.38 (2H, q), 1.36 (3H, t).

Reference Preparation Example 12

A mixture of the Intermediate compound B-7 (1.0 g), cyclopropylboronicacid (0.96 g), [1,1-bis(diphenylphosphino)ferrocene]palladium(II)dichloride (0.13 g), tripotassium phosphate (2.3 g), water (0.5 mL), andDME (5 mL) was stirred at 80° C. for 4 hours. The resulting mixture wascooled to room temperature, water was added thereto, and the resultingmixture was extracted with ethyl acetate. The resulting organic layerwas washed with saturated brine, dried over anhydrous sodium sulfate,and concentrated under reduced pressure. The resulting residue wassubjected to silica gel chromatography to give the Intermediate compoundB-8 represented by the following formula (0.27 g).

Intermediate compound B-8: ¹H-NMR (CDCl₃) δ: 8.24 (1H, s), 7.95 (1H,dd), 3.35 (2H, q), 2.03-1.96 (1H, m), 1.33 (3H, t), 1.15-1.12 (2H, m),0.80-0.77 (2H, m).

Reference Preparation Example 17

The Intermediate compounds which may be prepared according to themethods described in the Reference Preparation Examples 1 to 16 areshown below.

A compound represented by formula (C-7)

wherein the combination of R^(Q), R^(Q2), R^(3b), and R^(3c) representsany one combination indicated in [Table C7].

TABLE C7 Intermediate compound R^(Q) r^(Q2) R^(3b) R^(3c) B-13 OH SEtc-Pr H B-14 OH S(O)Et c-Pr H B-15 OH S(O)₂Et c-Pr H B-16 Cl SEt c-Pr HB-17 Cl S(O)Et c-Pr H B-18 Cl S(O)₂Et c-Pr H B-19 SEt SEt Cl H B-20S(O)₂Et S(O)₂Et Cl H B-21 Cl SEt Cl H B-22 Cl S(O)Et Cl H B-23 ClS(O)₂Et Cl H B-24 OH SEt Cl H B-25 OH S(O)Et Cl H B-26 OH S(O)₂Et Cl HB-27 Cl Cl c-Pr H B-28 F F c-Pr H B-29 F SEt Cl H B-30 F S(O)Et Cl HB-31 F S(O)₂Et Cl H B-32 F SEt c-Pr H B-33 F S(O)Et c-Pr H B-34 OHS(O)₂Et Br H

Intermediate compound B-16: ¹H-NMR (CDCl₃) δ: 7.93 (1H, d), 7.17 (1H,di), 2.95 (2H, q), 1.91-1.84 (1H, in), 1.37 (3H, t), 1.06-1.04 (2H, m),0.73-0.70 (2H, m).

Intermediate compound B-19: ¹H-NMR (CDCl₃) δ: 8.22 (1H, d), 7.42 (1H,d), 3.18 (2H, q), 2.96 (2H, q), 1.37-1.35 (6H, m).

Intermediate compound B-20: ¹H-NMR (CDCl₃) δ: 8.88 (1H, d), 8.60 (1H,d), 3.78 (2H, q), 3.64 (2H, q), 1.42 (3H, t), 1.37 (3H, t).

Intermediate compound B-23: ¹H-NMR (CDCl₃) δ: 8.59 (1H, d), 8.42 (1H,d), 3.51 (2H, q), 1.34 (3H, t).

Intermediate compound B-26: ¹H-NMR (CDCl₃) δ: 8.28 (1H, d), 7.87 (1H,d), 3.48 (2H, q), 1.32 (3H, t).

Intermediate compound B-28: ¹H-NMR (CDCl₃) δ: 7.78 (1H, s), 7.19-7.14(1H, m), 1.95-1.88 (1H, m), 1.07-1.04 (2H, m), 0.71-0.68 (2H, m).

Intermediate compound B-31: ¹H-NMR (CDCl₃) δ: 8.43 (1H, dd), 8.35 (1H,m), 3.40 (2H, q), 1.36 (3H, t).

Reference Preparation Example 18

A mixture of the Present compound 9 (225 mg), bis(pinacolato)diboron(253 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(18 mg), potassium acetate (147 mg), and toluene (1.7 mL) was stirred at80° C. for 1 hour. To the resulting mixture was added water underice-cooling, and the resulting mixture was extracted with ethyl acetate.The resulting organic layer was dried over anhydrous sodium sulfate, andconcentrated under reduced pressure to give the Intermediate compoundD-1 as a crude product.

Intermediate compound D-1: ¹H-NMR (CDCl₃) δ: 9.13 (1H, d), 8.79 (1H, d),8.07 (1H, s), 7.23-7.16 (1H, d), 6.80 (1H, d), 3.43-3.40 (2H, m),1.31-1.26 (15H, m).

Preparation Example 1

Under nitrogen atmosphere, to a mixture of the Intermediate compound A-1(0.2 g), sodium hydride (oily, 60%) (0.05 g), and DMF (3 mL) was addedthe Intermediate compound B-2 (0.22 g) under ice-cooling, and theresulting mixture was stirred at 90° C. for 5 hours. The resultingmixture was cooled to room temperature, water was added thereto, and theresulting mixture was extracted with ethyl acetate. The resultingorganic layer was dried over anhydrous sodium sulfate, and thenconcentrated under reduced pressure. The resulting residue was subjectedto silica gel column chromatography (chloroform:methanol=10:1) to givethe Present compound 4 represented by the following formula (0.2 g).

Present compound 4: ¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.49 (1H, dd), 8.08(1H, s), 7.77 (1H, dd), 7.23 (1H, d), 6.81 (1H, d), 3.40 (2H, q), 1.38(3H, t).

Preparation Example 1A

The compounds prepared according to the Preparation Example 1 and thephysical properties thereof are shown below.

A compound represented by formula (C-1)

wherein the combination of R¹, A², A³, R^(3b), R^(3c), and n representsany one combination indicated in [Table C1].

TABLE C1 Present compound R¹ A² A³ R^(3b) R^(3b) n 1 CF₃ CH CH H H 2 2CF₃ CH CH c-Pr H 2 3 CF₃ CH CH CF₃ H 2

Present compound 1: ¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.48 (1H, dd), 7.78(1H, s), 7.72 (1H, dd), 7.24 (1H, d), 6.93 (1H, d), 3.52-3.46 (2H, m),1.36 (3H, t).

Present compound 2: ¹H-NMR (CDCl₃) δ: 8.59 (1H, d), 8.01 (1H, d), 7.77(1H, d), 7.23 (1H, d), 6.87 (1H, d), 3.43 (2H, q), 2.08-2.07 (1H, m),1.34 (3H, t), 1.28-1.23 (2H, m), 0.94-0.88 (2H, m).

Present compound 3: ¹H-NMR (CDCl₃) δ: 9.11 (1H, dd), 8.67 (1H, d), 7.82(1H, s), 7.32 (1H, d), 6.96 (1H, d), 3.56 (2H, q), 1.40 (3H, t).

A compound represented by formula (C-2)

wherein the combination of R¹, A², A³, R^(3b), R^(3c), and n representsany one combination indicated in [Table C2].

TABLE C2 Present compound R¹ A² A³ R^(3b) R^(3c) n 5 CF₃ CH CH c-Pr H 26 CF₃ CH CH CF₃ H 2 9 CF₃ CH CH Br H 2 15 C₂F₅ CH CH H H 2 16 C₂F₅ CH CHBr H 2 17 C₂F₅ CH CH c-Pr H 2

Present compound 5: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.07 (1H, s), 8.02(1H, d), 7.18 (1H, d), 6.78 (1H, d), 3.35 (2H, q), 2.14-2.07 (1H, m),1.36 (3H, t), 1.30-1.26 (2H, m), 0.95-0.91 (2H, m).

Present compound 6: ¹H-NMR (CDCl₃) δ: 9.13 (1H, d), 8.69 (1H, d), 8.09(1H, s), 7.25 (1H, d), 6.85 (1H, d), 3.52-3.46 (2H, m), 1.43 (3H, t).

Present compound 9: ¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.58 (1H, d), 8.07(1H, s), 7.19 (1H, d), 6.81 (1H, d), 3.42 (2H, m), 1.40 (3H, t).

Present compound 15: ¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.50 (1H, dd),8.12 (1H, s), 7.77 (1H, dd), 7.23 (1H, d), 6.83 (1H, d), 3.44-3.39 (2H,m), 1.39 (3H, t).

Present compound 16: ¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.58 (1H, d), 8.12(1H, s), 7.22 (1H, d), 6.83 (1H, d), 3.43 (2H, q), 1.39 (3H, t).

Present compound 17: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.10 (1H, s), 8.02(1H, d), 7.18 (1H, d), 6.80 (1H, d), 3.35 (2H, q), 2.13-2.08 (1H, m),1.36 (3H, t), 1.31-1.24 (2H, m), 0.98-0.89 (2H, m).

A compound represented by formula (C-3)

wherein the combination of R¹, R^(6a), A², A³, R^(3b), R^(3c), and nrepresents any one combination indicated in [Table C3].

TABLE C3 Present compound R¹ R^(6 a) A² A³ R^(3b) R^(3c) n 7 CF₃ H CH CHH H 2 8 CF₃ H CH CH c-Pr H 2 22 CF₃ H CH CBr c-Pr H 2 23 CF₃ H CH CClc-Pr H 2 24 CF₃ Br CH CH c-Pr H 2 25 CF₃ Cl CH CH c-Pr H 2

Present compound 7: ¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.49 (1H, dd), 7.73(1H, dd), 7.60 (1H, dd), 7.39 (1H, s), 6.90 (1H, d), 3.41 (2H, m), 1.36(3H, t).

Present compound 8: ¹H-NMR (CDCl₃) δ: 8.61 (1H, d), 8.02 (1H, d), 7.58(1H, d), 7.38 (1H, s), 6.85 (1H, d), 3.36 (2H, q), 2.10 (1H, m), 1.34(3H, t), 1.26 (2H, m), 0.93 (2H, m).

Present compound 22: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.01 (1H, d), 7.52(1H, s), 7.07 (1H, s), 3.37 (2H, q), 2.10 (1H, m), 1.35 (3H, t), 1.27(2H, m), 0.92 (2H, m).

Present compound 23: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.01 (1H, d), 7.49(1H, s), 7.00 (1H, s), 3.37 (2H, q), 2.09 (1H, m), 1.35 (3H, t), 1.27(2H, m), 0.92 (2H, m).

Present compound 24: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.01 (1H, d), 7.51(1H, d), 6.85 (1H, d), 3.39 (2H, m), 2.09 (1H, m), 1.36 (3H, t), 1.26(2H, m), 0.92 (2H, m).

Present compound 25: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.01 (1H, d), 7.47(1H, d), 6.83 (1H, d), 3.39 (2H, m), 2.09 (1H, m), 1.36 (3H, t), 1.26(2H, m), 0.92 (2H, m).

the Present compound 18: ¹H-NMR (CDCl₃) δ: 8.90 (1H, dd), 8.50 (1H, dd),7.77 (1H, dd), 7.33 (1H, d), 7.00 (1H, d), 3.47 (2H, q), 1.39 (3H, t).

Present compound 19: ¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.02 (1H, d), 7.30(1H, d), 6.94 (1H, d), 3.41 (2H, m), 2.10 (1H, m), 1.36 (3H, t), 1.27(2H, m), 0.92 (2H, m).

Present compound 20: ¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.51 (1H, dd),7.81 (1H, dd), 7.52 (1H, d), 6.93 (1H, d), 3.47 (2H, q), 1.39 (3H, t).

Present compound 21: ¹H-NMR (CDCl₃) δ: 8.61 (1H, d), 8.02 (1H, d), 7.46(1H, d), 6.90 (1H, d), 3.42 (2H, m), 2.12 (1H, m), 1.37 (3H, t), 1.30(2H, m), 0.94 (2H, m).

Preparation Example 2

A mixture of the Present compound 9 (0.3 g), 4-fluorophenylboronic acid(186 mg), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride(51.3 mg), tripotassium phosphate (423 mg), water (0.3 mL), and DME (3.3mL) was stirred at 80° C. for 2 hours. The resulting mixture was cooledto room temperature, water was added thereto, and the resulting mixturewas extracted with ethyl acetate. The resulting organic layer was washedwith saturated brine, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography (hexane ethyl acetate=1:1) to give thePresent compound 10 represented by the following formula (0.14 g).

Present compound 10: ¹H-NMR (CDCl₃) δ: 9.02-9.00 (1H, m), 8.57-8.56 (1H,m), 8.10 (1H, s), 7.68-7.65 (2H, m), 7.30-7.24 (3H, m), 6.82 (1H, d),3.43 (2H, q), 1.41 (3H, m).

Preparation Example 3

To the crude product of the Intermediate compound D-1 prepared in theReference Preparation Example 18 were added water (1.6 mL), THE (0.4mL), and sodium acetate (307 mg), and hydrogen peroxide (35% aqueoussolution) was added dropwise thereto under ice-cooling. The resultingmixture was stirred under ice-cooling for 2 hours, a 1 M aqueoussolution of sodium thiosulfate and a saturated aqueous solution ofammonium chloride were added thereto, and then the resulting mixture wasextracted with ethyl acetate. The resulting organic layer was washedwith a 1 M aqueous solution of sodium thiosulfate and saturated brine,dried over anhydrous sodium sulfate, and then concentrated under reducedpressure to give the Present compound 26.

Present compound 26: ¹H-NMR (CDCl₃) δ: 8.45 (1H, br s), 8.08 (1H, s),7.90 (1H, brs), 7.18 (1H, d), 6.77 (1H, d), 3.33 (2H, q), 1.35 (3H, t).

Preparation Example 4

To the Present compound 26 prepared in the Preparation Example 3 wereadded DMF (1.7 mL), cesium carbonate (244 mg), and iodoethane (0.06 mL),and the resulting mixture was stirred at room temperature for 1 hour. Tothe resulting mixture were added water and a saturated aqueous solutionof ammonium chloride, and the resulting mixture was extracted with ethylacetate. The resulting organic layer was dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residuewas subjected to silica gel chromatography (hexane:ethyl acetate=1:3) togive the Present compound 11 represented by the following formula (0.1g).

Present compound 11: ¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.07 (1H, s), 7.87(1H, d), 7.16 (1H, d), 6.77 (1H, d), 4.28-4.22 (2H, m), 3.34 (2H, q),1.53 (3H, t), 1.36 (3H, t).

Preparation Example 4A

The compounds prepared according to the Preparation Example 4 and thephysical properties thereof are shown below.

Present compound 12: ¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.07 (1H, s), 7.85(1H, d), 7.16 (1H, d), 6.77 (1H, d), 4.78-4.72 (1H, m), 3.34 (2H, q),1.46 (6H, m), 1.37 (3H, t).

Present compound 13: ¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 8.07 (1H, s), 7.88(1H, d), 7.16 (1H, d), 6.77 (1H, dd), 4.13 (2H, q), 3.37-3.32 (2H, m),1.92 (2H, m), 1.37 (3H, t), 1.10 (3H, t).

Present compound 14: ¹H-NMR (CDCl₃) δ: 8.59 (1H, d), 8.07 (1H, s), 7.98(1H, d), 7.16 (1H, dd), 6.79 (1H, d), 4.59 (2H, q), 3.38 (2H, m), 1.38(3H, t).

Preparation Example 5

The compounds which can be prepared according to the methods describedin the Preparation Examples 1 to 4 are shown below.

A compound represented by formula (C-4)

wherein the combination of R¹, A², A³, R^(3b), R^(3c), and n representsany one combination indicated in [Table C4].

TABLE C4 Present compound R¹ A² A³ R^(3b) R^(3c) n 27 C₂F₅ CH CH H H 228 C₂F₅ CH CH c-Pr H 2 29 C₂F₅ CH CH CF₃ H 2 30 CF₃ CH N H H 2 31 CF₃ CHN c-Pr H 2 32 CF₃ CH N CF₃ H 2

A compound represented by formula (C-5)

wherein the combination of R¹, A², A³, R^(3b), R^(3c), and n representsany one combination indicated in [Table C5].

TABLE C5 Present compound R¹ A² A³ R^(3b) R^(3c) n 33 CF₃ CH N c-Pr H 234 C₂F₅ CH CH CF₃ H 2 35 CF₃ CH N CF₃ H 2 36 CF₃ CH N Br H 2 37 C₂F₅ CHN H H 2 38 C₂F₅ CH N Br H 2 39 C₂F₅ CH N c-Pr H 2

A compound represented by formula (C-6)

wherein the combination of R¹, R^(6a), A², A³, R^(3b), R^(3c), and nrepresents any one combination indicated in [Table C6].

TABLE C6 Present compound R¹ R^(6 a) A² A³ R^(3b) R^(3c) n 40 CF₃ H CH NH H 2 41 CF₃ H CH N c-Pr H 2 42 C₂F₅ H CH CH H H 2 43 C₂F₅ H CH CH c-PrH 2 44 CF₃ Br CH N c-Pr H 2 45 CF₃ Cl CH N c-Pr H 2 46 C₂F₅ Br CH CHc-Pr H 2 47 C₂F₅ Cl CH CH c-Pr H 2

Next, examples of the Present compounds prepared according to any one ofthe Preparation Examples described in Examples and the processesdescribed in the present description are shown below. In the followingexamples, Q11 to Q21 represent the following groups.

A compound represented by formula (L-1)

(hereinafter referred to as “Compound (L-1)”), wherein Q represents agroup represented by Q11, and R¹ represents any one substituentdescribed in [Table A1] or [Table A2](hereinafter referred to as“Compound group SX1”).

TABLE A1   CF₃ CHF₂ CH₂CF₃ CF₂CF₃ CH₂CF₂CF₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃CE₂CF₂CF₂CF₂CF₃ C (CF₃)₃ C(CH₃)₂CN OCF₃ OCHF₂ OCH₂CF₃ OCH₂CHF₂ OCF₂CF3OCH(CH₃)CF₃ OCH₂CF₂CHF₂ OCH₂CF₂CF₃ OCF₂CF₂CF₃ OCH₂CF₂CHFCF₃OCH₂CF₂CF₂CF₃ OCF₂CF₂CF₂CF₃ OCH₂CF₂CF₂CF₂CF₃ OS(O)₂CF₃ OS(O)₂CF₂CF₃OS(O)₂CF₂CF₂CF₃

TABLE A2   SCF₃ SCH₂CF₃ SCF₂CF₃ SCH₂CF₂CF₃ SCF₂CF₂CF₃ SCH₂CF₂CF₂CF₃SCF₂CF₂CF₂CF₃ S(O)CF₃ S(O)CH₂CF₃ S(O)CF₂CF₃ S(O)CH₂CF₂CF₃ S(O)CF₂CF₂CF₃S(O)CHCFCFCF₃ S(O)CF₂CF₂CF₂CF₃ S(O)₂CF₃ S(O)₂CH₂CF₃ S(O)₂CF₂CF₃S(O)₂CH₂CF₂CF₃ S(O)₂CF₂CF₂CF₃ S(O)₂CH₂CF₂CF₂CF₃ S(O)₂CF₂CF₂CF₂CF₃ c-Pr1-CN-c-Pr 2-CN-c-Pr 1-CN-C-Bu CF(CF₃)₂

The Compound (L-1), wherein Q represents a group represented by Q12, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX2”).

The Compound (L-1), wherein Q represents a group represented by Q13, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX3”).

The Compound (L-1), wherein Q represents a group represented by Q14, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX4”).

The Compound (L-1), wherein Q represents a group represented by Q15, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX5”).

The Compound (L-1), wherein Q represents a group represented by Q16, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX6”).

The Compound (L-1), wherein Q represents a group represented by Q17, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX7”).

The Compound (L-1), wherein Q represents a group represented by Q18, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX8”).

The Compound (L-1), wherein Q represents a group represented by Q19, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX9”).

The Compound (L-1), wherein Q represents a group represented by Q20, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX10”).

The Compound (L-1), wherein Q represents a group represented by Q21, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX11”).

In the following examples, Q31 to Q52 represent the following groups.

A compound represented by formula (L-2)

(hereinafter referred to as “Compound (L-2)”), wherein Q represents agroup represented by Q31, R^(3b) represents any one substituentdescribed in [Table A3] to [Table A11], and R^(3c) represents a hydrogenatom (hereinafter referred to as “Compound group SX12”).

TABLE A3   F Cl Br Me Et Pr i-Pr c-Pr 1-CN-c-Pr OMe OEt OPr Oi-Pr CF₃NH₂ NHCH₂CF₃ CN C(O)OEt NHC(O)c-Pr NMeC(O)c-Pr CH═N—OH CH═N—OMe

TABLE A4   Ph 3-F-Ph 4-F-Ph 3-Cl-Ph 4-Cl-Ph 3-CF₃-Ph 4-CF₃-Ph 3-NMe₂-Ph4-NMe₂-Ph 3-CN-Ph 4-CN-Ph 4-C(O)NMe₂-Ph 4-NHC(O)Me-Ph 3,4-F₂-Ph3,5-F₂-Ph 2,4-F₂-Ph 3,4,5-F₃-Ph 3,4-Cl₂-Ph 3,5-Cl₂-Ph 3,5-Cl₂-4-F-Ph OPhO-2-F-Ph

TABLE A5   Py2 4-F-Py2 5-F-Py2 4-Cl-Py2 5-Cl-Py2 4-CF₃-Py2 5-CF₃-Py23-Me-Py2 4-Me-Py2 5-Me-Py2 6-Me-Py2 5-CN-Py2 5-OCH₂CF₂CF₃-Py2 3,5-F₂-Py2Py3 6-CF₃-Py3 5-CF₃-Py3 6-F-Py3 6-Cl-Py3 Py4 OPy2 OPy3

TABLE A6

TABLE A7

TABLE A8

TABLE A9

TABLE A10

TABLE A11

Compound (L-2), wherein Q represents a group represented by Q31, R^(3b)represents a hydrogen atom, and R³, represents any one substituentdescribed in [Table A3] to [Table A11] (hereinafter referred to as“Compound group SX13”).

The Compound (L-2), wherein Q represents a group represented by Q32,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX14”).

The Compound (L-2), wherein Q represents a group represented by Q32,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX15”).

The Compound (L-2), wherein Q represents a group represented by Q33,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX16”).

The Compound (L-2), wherein Q represents a group represented by Q33,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX17”).

The Compound (L-2), wherein Q represents a group represented by Q34,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX18”).

The Compound (L-2), wherein Q represents a group represented by Q34,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX19”).

The Compound (L-2), wherein Q represents a group represented by Q35,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX20”).

The Compound (L-2), wherein Q represents a group represented by Q35,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX21”).

The Compound (L-2), wherein Q represents a group represented by Q36,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX22”).

The Compound (L-2), wherein Q represents a group represented by Q36,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX23”).

The Compound (L-2), wherein Q represents a group represented by Q37,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX24”).

The Compound (L-2), wherein Q represents a group represented by Q37,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX25”).

The Compound (L-2), wherein Q represents a group represented by Q38,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX26”).

The Compound (L-2), wherein Q represents a group represented by Q38,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX27”).

The Compound (L-2), wherein Q represents a group represented by Q39,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX28”).

The Compound (L-2), wherein Q represents a group represented by Q39,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX29”).

The Compound (L-2), wherein Q represents a group represented by Q40,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX30”).

The Compound (L-2), wherein Q represents a group represented by Q40,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX31”).

The Compound (L-2), wherein Q represents a group represented by Q41,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX32”).

The Compound (L-2), wherein Q represents a group represented by Q41,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX33”).

The Compound (L-2), wherein Q represents a group represented by Q42,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX34”).

The Compound (L-2), wherein Q represents a group represented by Q42,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX35”).

The Compound (L-2), wherein Q represents a group represented by Q43,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX36”).

The Compound (L-2), wherein Q represents a group represented by Q43,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX37”).

The Compound (L-2), wherein Q represents a group represented by Q44,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX38”).

The Compound (L-2), wherein Q represents a group represented by Q44,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX39”).

The Compound (L-2), wherein Q represents a group represented by Q45,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX40”).

The Compound (L-2), wherein Q represents a group represented by Q45,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX41”).

The Compound (L-2), wherein Q represents a group represented by Q46,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX42”).

The Compound (L-2), wherein Q represents a group represented by Q46,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX43”).

The Compound (L-2), wherein Q represents a group represented by Q47,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX44”).

The Compound (L-2), wherein Q represents a group represented by Q47,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX45”).

The Compound (L-2), wherein Q represents a group represented by Q48,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX46”).

The Compound (L-2), wherein Q represents a group represented by Q48,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX47”).

The Compound (L-2), wherein Q represents a group represented by Q49,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX48”).

The Compound (L-2), wherein Q represents a group represented by Q49,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX49”).

The Compound (L-2), wherein Q represents a group represented by Q50,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX50”).

The Compound (L-2), wherein Q represents a group represented by Q50,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX51”).

The Compound (L-2), wherein Q represents a group represented by Q51,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX52”).

The Compound (L-2), wherein Q represents a group represented by Q51,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX53”).

The Compound (L-2), wherein Q represents a group represented by Q52,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX54”).

The Compound (L-2), wherein Q represents a group represented by Q52,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX55”).

A compound represented by formula (L-3)

(hereinafter referred to as “Compound (L-3)”), wherein Q represents agroup represented by Q11, and R¹ represents any one substituentdescribed in [Table A1] or [Table A2](hereinafter referred to as“Compound group SX56”).

The Compound (L-3), wherein Q represents a group represented by Q12, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX57”).

The Compound (L-3), wherein Q represents a group represented by Q13, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX58”).

The Compound (L-3), wherein Q represents a group represented by Q14, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX59”).

The Compound (L-3), wherein Q represents a group represented by Q15, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX60”).

The Compound (L-3), wherein Q represents a group represented by Q16, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX61”).

The Compound (L-3), wherein Q represents a group represented by Q17, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX62”).

The Compound (L-3), wherein Q represents a group represented by Q18, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX63”).

The Compound (L-3), wherein Q represents a group represented by Q19, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX64”).

The Compound (L-3), wherein Q represents a group represented by Q20, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX65”).

The Compound (L-3), wherein Q represents a group represented by Q21, andR¹ represents any one substituent described in [Table A1] or [Table A2](hereinafter referred to as “Compound group SX66”).

A compound represented by formula (L-4)

(hereinafter referred to as “Compound (L-4)”), wherein Q represents agroup represented by Q31, R^(3b) represents any one substituentdescribed in [Table A3] to [Table A11], and R^(3c) represents a hydrogenatom (hereinafter referred to as “Compound group SX67”).

The Compound (L-4), wherein Q represents a group represented by Q31,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX68”).

The Compound (L-4), wherein Q represents a group represented by Q32,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX69”).

The Compound (L-4), wherein Q represents a group represented by Q32,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX70”).

The Compound (L-4), wherein Q represents a group represented by Q33,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(j)C represents a hydrogen atom (hereinafter referred to as“Compound group SX71”).

The Compound (L-4), wherein Q represents a group represented by Q33,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX72”).

The Compound (L-4), wherein Q represents a group represented by Q34,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX73”).

The Compound (L-4), wherein Q represents a group represented by Q34,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX74”).

The Compound (L-4), wherein Q represents a group represented by Q35,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX75”).

The Compound (L-4), wherein Q represents a group represented by Q35,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX76”).

The Compound (L-4), wherein Q represents a group represented by Q36,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX77”).

The Compound (L-4), wherein Q represents a group represented by Q36,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX78”).

The Compound (L-4), wherein Q represents a group represented by Q37,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX79”).

The Compound (L-4), wherein Q represents a group represented by Q37,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX80”).

The Compound (L-4), wherein Q represents a group represented by Q38,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(j)C represents a hydrogen atom (hereinafter referred to as“Compound group SX81”).

The Compound (L-4), wherein Q represents a group represented by Q38,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX82”).

The Compound (L-4), wherein Q represents a group represented by Q39,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX83”).

The Compound (L-4), wherein Q represents a group represented by Q39,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX84”).

The Compound (L-4), wherein Q represents a group represented by Q40,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX85”).

The Compound (L-4), wherein Q represents a group represented by Q40,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX86”).

The Compound (L-4), wherein Q represents a group represented by Q41,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX87”).

The Compound (L-4), wherein Q represents a group represented by Q41,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX88”).

The Compound (L-4), wherein Q represents a group represented by Q42,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX89”).

The Compound (L-4), wherein Q represents a group represented by Q42,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX90”).

The Compound (L-4), wherein Q represents a group represented by Q43,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(j)C represents a hydrogen atom (hereinafter referred to as“Compound group SX91”).

The Compound (L-4), wherein Q represents a group represented by Q43,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX92”).

The Compound (L-4), wherein Q represents a group represented by Q44,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX93”).

The Compound (L-4), wherein Q represents a group represented by Q44,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX94”).

The Compound (L-4), wherein Q represents a group represented by Q45,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX95”).

The Compound (L-4), wherein Q represents a group represented by Q45,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX96”).

The Compound (L-4), wherein Q represents a group represented by Q46,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX97”).

The Compound (L-4), wherein Q represents a group represented by Q46,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX98”).

The Compound (L-4), wherein Q represents a group represented by Q47,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX99”).

The Compound (L-4), wherein Q represents a group represented by Q47,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX100”).

The Compound (L-4), wherein Q represents a group represented by Q48,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(j)C represents a hydrogen atom (hereinafter referred to as“Compound group SX101”).

The Compound (L-4), wherein Q represents a group represented by Q48,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX102”).

The Compound (L-4), wherein Q represents a group represented by Q49,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX103”).

The Compound (L-4), wherein Q represents a group represented by Q49,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX104”).

The Compound (L-4), wherein Q represents a group represented by Q50,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX105”).

The Compound (L-4), wherein Q represents a group represented by Q50,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX106”).

The Compound (L-4), wherein Q represents a group represented by Q51,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX107”).

The Compound (L-4), wherein Q represents a group represented by Q51,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX108”).

The Compound (L-4), wherein Q represents a group represented by Q52,R^(3b) represents any one substituent described in [Table A3] to [TableA11], and R^(3c) represents a hydrogen atom (hereinafter referred to as“Compound group SX109”).

The Compound (L-4), wherein Q represents a group represented by Q52,R^(3b) represents a hydrogen atom, and R^(3c) represents any onesubstituent described in [Table A3] to [Table A11] (hereinafter referredto as “Compound group SX110”).

Next, Formulation Examples of the Present compound X are shown below.The “part(s)” represents “part(s) by weight”. Also, the expression of“Present compound S” represents the compounds described in the Compoundgroups SX1 to SX110.

Formulation Example 1

Any one of the Present compound S (10 parts) is mixed with a mixture ofxylene (35 parts) and DMF (35 parts), and then polyoxyethylene styrylphenyl ether (14 parts) and calcium dodecylbenzene sulfonate (6 parts)are added thereto, followed by mixing them to obtain each formulation.

Formulation Example 2

Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), wetsilica (20 parts), and diatomaceous earth (54 parts) are mixed, andfurther any one of the Present compound S (20 parts) is added thereto,followed by mixing them to obtain each formulation.

Formulation Example 3

To any one of the Present compound S (2 parts) are added wet silica (1part), calcium lignin sulfonate (2 parts), bentonite (30 parts), andkaolin clay (65 parts), followed by mixing them to obtain a mixture. Tothe mixture is then added an appropriate amount of water, the resultingmixture is additionally stirred, and subjected to granulation with agranulator and forced-air drying to obtain each formulation.

Formulation Example 4

Any one of the Present compound S (1 part) is mixed with an appropriateamount of acetone, and then wet silica (5 parts), acidic isopropylphosphate (0.3 part), and kaolin clay (93.7 parts) are added thereto,followed by mixing with stirring thoroughly and removal of acetone fromthe mixture by evaporation to obtain each formulation.

Formulation Example 5

A mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wetsilica (weight ratio of 1:1) (35 parts), any one of the Present compoundS (20 parts), and water (45 parts) are thoroughly mixed to obtain eachformulation.

Formulation Example 6

Any one of the Present compound S (0.1 part) is mixed with a mixture ofxylene (5 parts) and trichloroethane (5 parts), and the resultingmixture is then mixed with kerosene (89.9 parts) to obtain eachformulation.

Formulation Example 7

Any one of the Present compound S (10 mg) is mixed with acetone (0.5mL), and the solution is added dropwise to a solid feed powder for ananimal (solid feed powder for rearing and breeding CE-2, manufactured byCLEA Japan, Inc.) (5 g), followed by mixing the resulting mixtureuniformly, and then by drying it by evaporation of acetone to obtaineach poison bait.

Formulation Example 8

Any one of the Present compound S (0.1 part) and Neothiozole(manufactured by Chuo Kasei Co., Ltd.) (49.9 parts) are placed into anaerosol can. After mounting an aerosol valve, dimethyl ether (25 parts)and LPG (25 parts) are filled, followed by shaking and further mountingan actuator to obtain each oily aerosol.

Formulation Example 9

A mixture of any one of the Present compound S (0.6 part),2,6-di-tert-butyl-4-methylphenol (0.01 part), xylene (5 parts), kerosene(3.39 parts), and Rheodol (registered trademark) MO-60 (1 part), anddistilled water (50 parts) are filled into an aerosol container, and avalve part is attached. Then, LPG (40 parts) is filled therein throughthe valve to obtain each aqueous aerosol.

Formulation Example 10

Any one of the Present compound S (0.1 g) is mixed with propylene glycol(2 mL), and the resulting solution is impregnated into a ceramic platehaving a size of 4.0 cm×4.0 cm and a thickness of 1.2 cm to obtain eachthermal smoking agent.

Formulation Example 11

Any one of the Present compound S (5 parts) and ethylene-methylmethacrylate copolymer (the ratio of the methyl methacrylate relative tothe total weight of the copolymer: 10% by weight) (95 parts) are meltedand kneaded, and the resulting kneaded product is extruded from anextrusion molding machine to obtain each rod-shaped molded producthaving a length of 15 cm and a diameter of 3 mm.

Formulation Example 12

Any one of the Present compound S (5 parts) and a flexible vinylchloride resin (95 parts) are melted and kneaded, and the resultingkneaded product is extruded from an extrusion molding machine to obtaineach rod-shaped molded product having a length of 15 cm and a diameterof 3 mm.

Formulation Example 13

Any one of the Present compound S (100 mg), lactose (68.75 mg), cornstarch (237.5 mg), microcrystalline cellulose (43.75 mg),polyvinylpyrrolidone (18.75 mg), sodium carboxymethyl starch (28.75 mg),and magnesium stearate (2.5 mg) are mixed, and the resulting mixture iscompressed to an appropriate size to obtain each tablet.

Formulation Example 14

Any one of the Present compound S (25 mg), lactose (60 mg), corn starch(25 mg), carmellose calcium (6 mg), and an appropriate amount of 5%hydroxypropyl methylcellulose are mixed, and the resulting mixture isfilled into a hard shell gelatin capsule or a hydroxypropylmethylcellulose capsule to obtain each capsule.

Formulation Example 15

To any one of the Present compound S (100 mg), fumaric acid (500 mg),sodium chloride (2,000 mg), methylparaben (150 mg), propylparaben (50mg), granulated sugar (25,000 mg), sorbitol (70% solution) (13,000 mg),Veegum (registered trademark) K (100 mg), perfume (35 mg), and colorant(500 mg) is added distilled water so that the final volume is set to be100 mL, followed by mixing them to obtain each suspension for oraladministration.

Formulation Example 16

Any one of the Present compound S (5 parts) is mixed with an emulsifier(5 parts), benzyl alcohol (3 parts), and propylene glycol (30 parts),and phosphate buffer is added thereto so that the pH of the solution isset to be 6.0 to 6.5, and then water is added thereto as the rest partsto obtain each solution for oral administration.

Formulation Example 17

Aluminum distearate (5 parts) is added to fractional distillated coconutoil (57 parts) and polysorbate 85 (3 parts), and dispersed by heating.The resulting mixture is cooled to room temperature, and saccharin (25parts) is dispersed in the oil vehicle. Any one of the Present compoundS (10 parts) is distributed thereto to obtain each paste-likeformulation for oral administration.

Formulation Example 18

Any one of the Present compound S (5 parts) is mixed with a limestonefiller (95 parts), followed by a wet granulation of the resultingmixture to obtain each granule for oral administration.

Formulation Example 19

Any one of the Present compound S (5 parts) is mixed with diethyleneglycol monoethyl ether (80 parts), propylene carbonate (15 parts) isadded thereto, and the resulting mixture is mixed to obtain each spot-onsolution.

Formulation Example 20

Any one of the Present compound S (10 parts) is mixed with diethyleneglycol monoethyl ether (70 parts), 2-octyldodecanol (20 parts) is addedthereto, and the resulting mixture is mixed to obtain each pour-onsolution.

Formulation Example 21

Any one of the Present compound S (0.1 part), sodium polyoxyethylenelauryl ether sulfate (25% aqueous solution) (40 parts), lauramidopropylbetaine (5 parts), coconut oil fatty acid ethanolamide (5 parts),carboxyvinyl polymer (0.5 part), and purified water (49.4 parts) arethoroughly mixed to obtain each shampoo formulation.

Formulation Example 22

Any one of the Present compound S (0.15 part), an animal feed (95parts), and a mixture (4.85 parts) consisting of calcium hydrogenphosphate, diatomaceous earth, Aerosil (registered trademark), andcarbonate (or chalk) are mixed with stirring thoroughly to obtain eachpremix for an animal feed.

Formulation Example 23

Any one of the Present compound S (7.2 g) and Hosco (registeredtrademark) S-55 (92.8 g) are mixed at 100° C., and the resulting mixtureis poured into a suppository mold, followed by performing a coolingsolidification to obtain each suppository.

Next, Test Examples are used to show effects of the Present compounds Xon harmful arthropods. In the following Test Examples, the tests werecarried out at 25° C.

Test Method 1

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and watercontaining Sindaine (registered trademark) (0.03% by volume) is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Cucumber (Cucumis sativus) seedlings (on the developmental stage of thesecond true leaf) are planted in a container and approximately 30 cottonaphids (Aphis gossypii) (all stages of life) are released onto thecucumber seedlings. After 1 day, each of said diluted solutions issprayed into the seedlings in a ratio of 10 mL/seedling. Afteradditional 5 days, the number of the surviving insects is examined andthe controlling value is calculated by the following equation.

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols in the equation represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group

Here the “untreated group” represents a group where a similar treatmentprocedure to that of the treated group except not using each testcompound is done.

Test Example 1-1

When the prescribed concentration was 500 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 1, each of the following Present compoundsshowed 90% or greater as the controlling value.

Present compounds: 1, 2, 3, 4, 5, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17,20, 22, 23, and 25

Test Example 1-2

When the prescribed concentration was 200 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 1, each of the following Present compoundsshowed 90% or greater as the controlling value.

Present compounds: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15,16, 17, 20, 21, 22, 23, 24, and 25

Test Method 2

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Cucumber seedlings (on the developmental stage of the second true leaf)are planted in a container, and each of said diluted solutions isirrigated into the plant foot in a ratio of 5 mL/seedling. After 7 days,approximately 30 cotton aphids (Aphis gossypii) (all stages of life) arereleased onto the surfaces of leaves of the cucumber seedlings. Afteradditional 6 days, the number of the surviving insects is examined andthe controlling value is calculated by the following equation.

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols in the equation represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group

Here the “untreated group” represents a group where a similar treatmentprocedure to that of the treated group except not using each testcompound is done.

Test Example 2

When the prescribed concentration was 1000 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 2, each of the following Present compoundsshowed 90% or greater as the controlling value.

Present compounds: 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16,17, 21, and 24

Test Method 3

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and watercontaining Sindaine (registered trademark) (0.03% by volume) is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Cabbage (Brassicae oleracea) seedlings (on the developmental stage ofthe second to third true leaf) are planted in a container, and each ofsaid diluted solutions is sprayed into the seedlings in a ratio of 20mL/seedling. Thereafter, the stem and leaf of the seedlings are cut out,and placed into a container lined with a filter paper. Five (5) the 2ndinstar larvae of diamondback moth (Plutella xylostella) are releasedinto the container. After 5 days, the number of the surviving insects iscounted, and the mortality of insects is calculated by the followingequation.

Mortality (%)=(1−Number of surviving insects/5)×100

Test Example 3

When the prescribed concentration was 500 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 3, each of the following Present compoundsshowed 80% or greater as the mortality.

Present compounds: 2, 4, 5, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 20,22, 23, and 25

Test Method 4

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and watercontaining a spreader (0.03% by volume) is added thereto to prepare adiluted solution containing a prescribed concentration of each testcompound.

Cabbage (Brassicae oleracea) seedlings (on the developmental stage ofthe third to fourth true leaf) are planted in a container, and each ofsaid diluted solutions is sprayed into the seedlings in a ratio of 20mL/seedling. Thereafter, 10 the 3rd instar larvae of diamondback moth(Plutella xylostella) are released into the cabbage seedlings. After 5days, the number of the surviving insects is counted, and the mortalityof insects is calculated by the following equation.

Mortality (%)=(1−Number of surviving insects/10)×100

Test Example 4

When the prescribed concentration was 200 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 4, each of the following Present compoundsshowed 90% or greater as the mortality.

Present compounds: 4, 5, 6, 8, 9, 10, 11, 12, 13, 15, 17, 21, 22, 23,24, and 25

Test Method 5

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and watercontaining Sindaine (registered trademark) (0.03% by volume) is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Cabbage (Brassicae oleracea) seedlings (on the developmental stage ofthe second to third true leaf) are planted in a container, and each ofsaid diluted solutions is sprayed into the seedlings in a ratio of 20mL/seedling. Thereafter, the stem and leaf of the seedlings are cut out,and placed into a container lined with a filter paper. Five (5) the 2ndinstar larvae of cotton worm (Spodoptera litura) are released into thecontainer. After 5 days, the number of the surviving insects is counted,and the mortality of insects is calculated by the following equation.

Mortality (%)=(1−Number of surviving insects/5)×100

Test Example 5

When the prescribed concentration was 500 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 5, each of the following Present compoundsshowed 80% or greater as the mortality.

Present compounds: 5, 7, 9, 10, 11, 12, 13, 14, 15, 16, and

Test Method 6

Each test compound is dissolved into a mixed solution (50 μL) ofpolyoxyethylene sorbitan mono-cocoate and acetone (at a volume ratio ofpolyoxyethylene sorbitan mono-cocoate:acetone=5:95) per 1 mg of the testcompound. Water containing Sindaine (registered trademark) (0.03% byvolume) is added thereto to prepare a diluted solution containing aprescribed concentration of each test compound.

Young seedlings of corns (Zea mays) are immersed into each of saiddiluted solutions for 30 seconds. Thereafter, two of said seedlings areplaced into a petri dish (diameter: 90 mm), and 10 the 2nd instar larvaeof western corn rootworm (Diabrotica virgifera virgifera) are releasedinto the dish. After 5 days, the number of the dead insects is counted,and the mortality of insects is calculated by the following equation.

Mortality (%)=(Number of dead insects/10)×100

Test Example 6

When the prescribed concentration was 500 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 6, each of the following Present compoundsshowed 80% or greater as the mortality.

Present compounds: 4, 5, 8, 9, 10, 14, 15, 16, 17, 21, 23, and 25

Test Method 7

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

A filter paper having a diameter of 5.5 cm is lined with the insidebottom of a cup having a diameter of 5.5 cm, each of said dilutedsolutions (0.7 mL) is added dropwise on the filter paper, and sucrose(30 mg) is homogeneously placed into said cup as a feed. Ten (10) femaleadult house flies (Musca domestica) are released into said cup, and thecup is covered. After 24 hours, life and death of the house flies areexamined, the number of the dead insects is counted, and the mortalityof insects is calculated by the following equation.

Mortality (%)=(Number of dead insects/Number of test insects)×100

Test Example 7

When the prescribed concentration was 500 ppm and each of the followingPresent compounds was used as a test compound to carry out a testaccording to the Test method 7, each of the following Present compoundsshowed 100% as the mortality.

Present compounds: 10, 11, 12, and 17

Test Method 8

Each test compound is formulated according to the process described inthe Formulation Example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

A filter paper having a diameter of 5.5 cm is lined with the insidebottom of a cup having a diameter of 5.5 cm, each of said dilutedsolutions (0.7 mL) is added dropwise on the filter paper, and sucrose(30 mg) is homogeneously placed into said cup as a feed. Two (2) maleadult German cockroaches (Blattella germanica) are released into saidcup, and the cup is covered. After 6 days, life and death of the Germancockroach are examined, the number of the dead insects is counted, andthe mortality of insects is calculated by the following equation.

Mortality (%)=(Number of dead insects/Number of test insects)×100

Test Example 8

When the prescribed concentration was 500 ppm and the following Presentcompound was used as a test compound to carry out a test according tothe Test method 8, the following Present compound showed 100% as themortality. Present compound: 12

Test Example 9

The Present compound (1 mg) is dissolved into a mixed solution (10 μL)of xylene, DMF, and surfactant (at a volume ratio ofxylene:DMF:surfactant=4:4:1), and the resulting solution is diluted withwater containing a spreader (0.02% by volume) to prepare a dilutedsolution A containing a prescribed concentration of the Presentcompound.

The Present ingredient (1 mg) is dissolved into a mixed solution (10 μL)of xylene, DMF, and surfactant (at a volume ratio ofxylene:DMF:surfactant=4:4:1), and the resulting solution is diluted withwater containing a spreader (0.02% by volume) to prepare a dilutedsolution B containing a prescribed concentration of the Presentingredient.

The diluted solution A and the diluted solution B are mixed to prepare adiluted solution C.

A lamina (length: 1.5 cm) of cucumber cotyledon is placed into each wellof a 24 well microplate, then two (2) wingless adults and eight (8)larvae of cotton aphids (Aphis gossypii) are released into each well,and 20 μL of the diluted solution C is sprayed into each well. Said wellis defined as “treated group”.

A well into which 20 μL of water containing a spreader (0.02% by volume)instead of the diluted solution C is sprayed is defined as “untreatedgroup”.

After the diluted solution C is dried, the upper part of the microplateis covered by a film sheet. After 5 days, the number of the survivinginsects in each well is examined.

The controlling value is calculated by the following equation.

Controlling value (%)={1−(Tai)/(Cai)}×100

wherein the symbols in the equation represent the following meanings.

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tai: Number of the surviving insects at the time of the investigation intreated group

Specific examples of the diluted solution C of which the effects can beconfirmed in the Test Example 9 include the following 1) to 5).

1) A diluted solution C of any one combination described in the List A,wherein the concentration of the Present compound is 200 ppm and theconcentration of the Present ingredient is 2,000 ppm. In the List A,Comp X represents any one compound selected from the Present compounds 1to 45.

List A:

Comp X+clothianidin; Comp X+thiamethoxam; Comp X+imidacloprid; CompX+thiacloprid; Comp X+flupyradifurone; Comp X+sulfoxaflor; CompX+triflumezopyrim; Comp X+dicloromezotiaz; Comp X+beta-cyfluthrin; CompX+tefluthrin; Comp X+fipronil; Comp X+chlorantraniliprole; CompX+cyantraniliprole; Comp X+tetraniliprole; Comp X+thiodicarb; CompX+carbofuran; Comp X+fluxametamide; Comp X+afoxolaner; CompX+fluralaner; Comp X+broflanilide; Comp X+abamectin; Comp X+fluopyram;Comp X+fluensulfone; Comp X+fluazaindolizine; Comp X+tioxazafen; CompX+flupyrimin; Comp X+mycorrhizal fungi; Comp X+Bradyrhizobium japonicumTA-11; Comp X+Bacillus firmus; Comp X+Bacillus firmus 1-1582; CompX+Bacillus amyloliquefaciens; Comp X+Bacillus amyloliquefaciens FZB42;Comp X+Pasteuria nishizawae; Comp X+Pasteuria nishizawae Pn1; CompX+Pasteuria penetrans; Comp X+tebuconazole; Comp X+prothioconazole; CompX+metconazole; Comp X+ipconazole; Comp X+triticonazole; CompX+difenoconazole; Comp X+imazalil; Comp X+triadimenol; CompX+tetraconazole; Comp X+flutriafol; Comp X+mandestrobin; CompX+azoxystrobin; Comp X+pyraclostrobin; Comp X+trifloxystrobin; CompX+fluoxastrobin; Comp X+picoxystrobin; Comp X+fenamidone; CompX+metalaxyl; Comp X+metalaxyl-M; Comp X+fludioxonil; Comp X+sedaxane;Comp X+penflufen; Comp X+fluxapyroxad; Comp X+benzovindiflupyr; CompX+boscalid; Comp X+carboxin; Comp X+penthiopyrad; Comp X+flutolanil;Comp X+captan; Comp X+thiram; Comp X+tolclofos-methyl; CompX+thiabendazole; Comp X+ethaboxam; Comp X+mancozeb; CompX+picarbutrazox; Comp X+oxathiapiprolin; Comp X+silthiofam; CompX+inpyrfluxam.

2) A diluted solution C of any one combination described in the List A,wherein the concentration of the Present compound is 200 ppm and theconcentration of the Present ingredient is 200 ppm.

3) A diluted solution C of any one combination described in the List A,wherein the concentration of the Present compound is 500 ppm and theconcentration of the Present ingredient is 50 ppm.

4) A diluted solution C of any one combination described in the List A,wherein the concentration of the Present compound is 500 ppm and theconcentration of the Present ingredient is 5 ppm.

5) A diluted solution C of any one combination described in the List A,wherein the concentration of the Present compound is 500 ppm and theconcentration of the Present ingredient is 0.5 ppm.

INDUSTRIAL APPLICABILITY

The Present compounds X have excellent control effects on harmfularthropods.

1. A compound of formula (C-7),

wherein R^(Q) represents a fluorine atom, a chlorine atom, or a—S(O)_(n)R²; R^(Q2) represents a —S(O)_(n)R² R² represents an ethylgroup; n represents 0, 1, or 2; R^(3b) represents a chlorine atom; andR^(3c) represents a hydrogen atom.
 2. The compound according to claim 1,which is a compound of formula B-21,

a compound of formula B-22,

a compound of formula B-23,

a compound of formula B-29,

a compound of formula B-30,

a compound of formula B-31,

a compound of formula B-19,

a compound of formula B-20


3. The compound according to claim 1, which is a compound of formulaB-21,


4. The compound according to claim 1, which is a compound of formulaB-22,


5. The compound according to claim 1, which is a compound of formulaB-23,


6. The compound according to claim 1, which is a compound of formulaB-29,


7. The compound according to claim 1, which is a compound of formulaB-30,


8. The compound according to claim 1, which is a compound of formulaB-31,


9. The compound according to claim 1, which is a compound of formulaB-19,


10. The compound according to claim 1, which is a compound of formulaB-20